August 25, 2021

The Ultimate Chicago City Guide: Flights & Tour info

Chicago Travel Guide

A beautiful, snow-filled wonderland, Chicago city exhibits a lively, welcoming ambiance. During the winter the city’s downtown and neighborhoods shine brightly with snowflakes. Chicago is the most populous city in the US state of Illinois and is located on the southwestern shores of Lake Michigan. When the Great Chicago Fire destroyed almost everything in the city, no one would have imagined that it would lead to the largest building boom in the history of America.

The city ushered in the skyscraper era with the construction of Chicago’s first steel-frame high-rise building, the Home Insurance Building. Following its construction, many other companies started building cloud kissing structures and soon the city’s skyline became impenetrable with such buildings. Chicago tourism recorded 55 million visitors in 2017. In 2016, Chicago saw 54.1 million visitors; a 2.9% increase from 2015. In 2015, it was estimated that 50.1 million visitors came to Chicago, which was a 4.5 percent increase from 2014.

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Quick Info

Country: USA
Total Area: 606.1 km2
Population: 27.1 lakhs (2019)
Language: English, the most common languages spoken in homes also Spanish, Polish, Arabic, Tagalog, and Chinese.
Currency: United States Dollars (USD)
Time Zone: Central (UTC-6), Summer (DST), Central (UTC-5)
Major Airport: O’Hare International Airport (ORD)
Major AirlinesHub for: – American Airlines & United Airlines
Focus city for Frontier Airlines &Spirit

Airlines flying from Chicago

In total there are 46 airlines flying from and to Chicago. Most flights are operated by one of the following carriers:

 United Airlines (UA) 213 destinations
American Airlines (AA) 168 destinations
Spirit Airlines (NK) 21 destinations
Frontier Airlines (F9) 19 destinations
Southwest Airlines (WN) 12 destinations
Delta Airlines (DL) 10 destinations
VivaAerobus (VB) 6 destinations
Alaska Airlines (AS) 6 destinations
Volaris Airlines(Y4) 5 destinations

Flights From Chicago

American Airlines flights from ChicagoChicago has a great network of flights to destinations all over the world. The following is an overview of all non-stop intercontinental flights operating from O’Hare International Airport (formerly Orchard Depot Fi (ORD).

Non-stop flights from Chicago to Europe: 

United Airlines (Star Alliance) has a significant network of flights from Chicago to Europe.

  • United Airlines – United Airlines (Star Alliance): year-round to Frankfurt (FRA), Munich (MUC), seasonal flights to Zürich (ZRH), Reykjavik (Keflavik) (KEF), Dublin (DUB), Edinburgh (EDI), year-round flights to London Heathrow (LHR), seasonal flights to Rome (Fiumicino) (FCO), year-round flights to Brussels (BRU), Paris (CDG) and Amsterdam (AMS).
  • Lufthansa – Lufthansa (Star Alliance): year-round to Frankfurt (FRA) and Munich (MUC).
  • Swiss – Swiss (Star Alliance): year-round to Zürich (ZRH).
  • LOT – LOT (Star Alliance): year-round to Krakow (KRK) and Warsaw (WAW).
  • Austrian – Austrian (Star Alliance): year-round to Vienna (VIE).
  • Icelandair – Icelandair: year-round to Reykjavik (Keflavik) (KEF).
  • American Airlines – American Airlines (Oneworld): seasonal flights to Dublin (DUB), year-round flights to London Heathrow (LHR), seasonal flights to Rome (Fiumicino) (FCO), Athens (ATH), Barcelona (BCN), and Paris (CDG).
  • Aer Lingus – Aer Lingus: year-round to Dublin (DUB).
  • British Airways – British Airways (Oneworld): year-round to London Heathrow (LHR).
  • SAS – SAS (Star Alliance): year-round to Copenhagen (CPH) and seasonal flights to Stockholm (Arlanda) (ARN).
  • Finnair – Finnair (Oneworld): year-round to Helsinki (HEL).
  • Iberia – Iberia (Oneworld): year-round to Madrid (MAD).
  • TAP Portugal – TAP Portugal (Star Alliance): year-round to Lisbon (LIS).
  • Air France – Air France (SkyTeam): year-round to Paris (CDG).
  • KLM – KLM (SkyTeam): year-round to Amsterdam (AMS).

Non-stop flights from Chicago to Canada

  • United Airlines – United Airlines (Star Alliance): seasonal flights to Calgary (YYC), Montreal (YUL), Ottawa (YOW), year-round flights to Toronto (YYZ), seasonal flights to Vancouver (YVR) and Winnipeg (YWG).
  • American Airlines – American Airlines (Oneworld): seasonal flights to Calgary (YYC), Montreal (YUL), year-round flights to Toronto (YYZ), and seasonal flights to Vancouver (YVR).
  • Air Canada – Air Canada (Star Alliance): year-round to Montreal (YUL), Toronto (YYZ), and seasonal flights to Vancouver (YVR).

Non-stop flights from Chicago to South America

  • United Airlines – United Airlines is currently the only airline flying non-stop from Chicago to Southern America. They fly year-round to São Paulo (GRU).

Non-stop flights from Chicago to Central America

  • United Airlines (Star Alliance) has a significant network of flights from Chicago to Central America.
  • United Airlines – United Airlines (Star Alliance): year-round to Belize City (BZE), Liberia (LIR), San José (SJO), Cancún (CUN), Cozumel (CZM), seasonal flights to Ixtapa / Zihuatanejo (ZIH), year-round flights to León (BJX), Mexico City (MEX), Monterrey (MTY), Puerto Vallarta (PVR) and San José del Cabo (SJD).
  • American Airlines – American Airlines (Oneworld): year-round to Cancún (CUN), seasonal flights to Cozumel (CZM), year-round flights to Puerto Vallarta (PVR), San José del Cabo (SJD) and Guatemala City (GUA).
  • Aeromexico – Aeromexico (SkyTeam): year-round to Guadalajara (GDL) and Mexico City (MEX).
  • Frontier Airlines – Frontier Airlines: year-round to Cancún (CUN) and seasonal flights to Cozumel (CZM).
  • Southwest Airlines – Southwest Airlines: seasonal flights to Cancún (CUN).
  • Spirit Airlines – Spirit Airlines: year-round to Cancún (CUN).
  • VivaAerobus – VivaAerobus: year-round to Guadalajara (GDL), seasonal flights to León (BJX), year-round flights to Mexico City (MEX), seasonal flights to Monterrey (MTY), Morelia (MLM) and Zacatecas (ZCL).
  • Volaris – Volaris: year-round to Guadalajara (GDL), León (BJX), Mexico City (MEX), Morelia (MLM) and Querétaro (QRO).
  • Copa Airlines – Copa Airlines (Star Alliance): year-round to Panama City (PTY).

Non-stop flights from Chicago to the Caribbean

  • United Airlines (Star Alliance) has a strong network of non-stop flights to the Caribbean.
  • United AirlinesUnited Airlines (Star Alliance): seasonal flights to Aruba (AUA), Nassau (NAS), Grand Cayman (GCM), year-round flights to Punta Cana (PUJ), Montego Bay (MBJ), San Juan (SJU), seasonal flights to Sint Maarten (SXM), Saint Lucia (UVF), Providenciales (PLS) and year-round flights to Saint Thomas (STT).
  • American Airlines – American Airlines (Oneworld): seasonal flights to Aruba (AUA), Nassau (NAS), Grand Cayman (GCM), Punta Cana (PUJ), Montego Bay (MBJ), year-round flights to San Juan (SJU), seasonal flights to Saint Lucia (UVF), Providenciales (PLS) and Saint Thomas (STT).
  • Frontier Airlines – Frontier Airlines: seasonal flights to Punta Cana (PUJ) and year-round flights to San Juan (SJU).

Non-stop flights from Chicago to Africa

  • Ethiopian Airlines – Ethiopian Airlines is currently the only airline flying non-stop from Chicago to Africa. They fly year-round to Addis Ababa (ADD).

Non-stop flights from Chicago to the Middle-East / Western Asia

  • United Airlines – United Airlines (Star Alliance): year-round to Tel Aviv (TLV).
  • EL AL – EL AL: seasonal flights to Tel Aviv (TLV).
  • Emirates – Emirates: year-round to Dubai (DXB).
  • Etihad Airways – Etihad Airways: year-round to Abu Dhabi (AUH).
  • Qatar Airways – Qatar Airways (Oneworld): year-round to Doha (DOH).
  • Royal Jordanian – Royal Jordanian (Oneworld): year-round to Amman (AMM).
  • Turkish Airlines – Turkish Airlines (Star Alliance): year-round to Istanbul (IST).

Non-stop flights from Chicago to India / South Asia

  • United Airlines – United Airlines (Star Alliance): year-round to New Delhi (DEL).
  • Air India – Air India (Star Alliance): year-round to Hyderabad (HYD) and New Delhi (DEL).
  • Non-stop flights from Chicago to China
    United Airlines – United Airlines is currently the only airline flying non-stop from Chicago to China. They fly seasonal to Beijing (PEK) and Shanghai (PVG).

Non-stop flights from Chicago to Japan

  • United Airlines – United Airlines (Star Alliance): year-round to Tokyo (HND).
  • ANA – ANA (Star Alliance): seasonal flights to Osaka (KIX), Tokyo (HND) and year-round flights to Tokyo (NRT).
  • Japan Airlines – Japan Airlines (Oneworld): year-round to Tokyo (HND) and seasonal flights to Tokyo (NRT).

Non-stop flights from Chicago to East Asia: Cathay Pacific

Cathay Pacific (Oneworld): year-round to Hong Kong (HKG).

  • EVA Air – EVA Air (Star Alliance): year-round to Taipei (TPE).
  • Korean Air – Korean Air (SkyTeam): year-round to Seoul (ICN).

Non-stop flights from Chicago to South-East Asia

  • Currently, there are no direct services between Chicago and South-Eastern Asia, you will need to change planes along the way.

Non-stop flights from Chicago to Central Asia

  • Currently, there are no direct services between Chicago and Central Asia, you will need to change planes along the way.

Non-stop flights from Chicago to Australia / New Zealand / Oceania / the Pacific

  • Air New Zealand – Air New Zealand is currently the only airline flying non-stop from Chicago to Oceania. They fly seasonally to Auckland (AKL).

International flights from Chicago

  • Flights from Chicago to Aruba: Aruba is the only destination in Aruba with direct flights from Chicago. You can fly non-stop to Aruba with American Airlines (Oneworld) or United Airlines (Star Alliance). This is a seasonal route that starts in August and ends in September.
  • Flights from Chicago to Austria
    In Austria, the only destination that has a direct flight from Chicago is Vienna. Direct flights to Vienna are offered by Austrian (Star Alliance).
  • Flights from Chicago to the Bahamas: There is 1 destination in the Bahamas that has a direct connection from Chicago, which is Nassau. You can fly non-stop to Nassau with American Airlines (Oneworld) or United Airlines (Star Alliance). This is a seasonal route that starts in August and ends in September.
  • Flights from Chicago to Belgium: In Belgium, the only destination that has a direct flight from Chicago is Brussels. Direct flights to Brussels are offered by United Airlines (Star Alliance).
  • Flights from Chicago to Belize: Belize City is the only destination in Belize with direct flights from Chicago. Direct flights to Belize City are offered by United Airlines (Star Alliance).
  • Flights from Chicago to Brazil: There is 1 destination in Brazil that has a direct connection from Chicago, which is São Paulo. Direct flights to São Paulo are offered by United Airlines (Star Alliance).
  • Flights from Chicago to Canada
    In Canada, there are several destinations from Chicago (6 in total).

    • You can fly non-stop to Calgary with American Airlines (Oneworld) or United Airlines (Star Alliance). This route is not operational yet but will start in October.
    • Non-stop flights to Montreal are offered by Air Canada (Star Alliance), American Airlines (Oneworld), and United Airlines (Star Alliance).
    • You can fly non-stop from Chicago to Ottawa with United Airlines (Star Alliance). This route is not operational yet but will start in October.
    • To Toronto and Vancouver, you can fly with Air Canada (Star Alliance), American Airlines (Oneworld), and United Airlines (Star Alliance).
    • You can fly non-stop from Chicago to Winnipeg with United Airlines (Star Alliance). This route is not operational yet but will start in October.
  • Cayman Islands Flights from Chicago to the Cayman Islands: Grand Cayman is the only destination in the Cayman Islands with direct flights from Chicago. You can fly non-stop to Grand Cayman with American Airlines (Oneworld) or United Airlines (Star Alliance). This is a seasonal route that starts in November and ends in June.
  • Flights from Chicago to China
    • There are 2 destinations in China that have non-stop flights from Chicago.
    • To Beijing and Shanghai, you can fly with United Airlines (Star Alliance).
  • Flights from Chicago to Costa Rica: If you are looking for a direct flight from Chicago to Costa Rica, there are 2 destinations to choose from.
  • To Liberia and San José, you can fly with United Airlines (Star Alliance).
  • Flights from Chicago to Denmark: In Denmark, the only destination that has a direct flight from Chicago is Copenhagen. Direct flights to Copenhagen are offered by SAS (Star Alliance).
  • Flights from Chicago to the Dominican Republic: There is 1 destination in the Dominican Republic that has a direct connection from Chicago, which is Punta Cana. Non-stop flights to Punta Cana are offered by American Airlines (Oneworld), Frontier Airlines, and United Airlines (Star Alliance).
  • Flights from Chicago to Ethiopia: In Ethiopia, the only destination that has a direct flight from Chicago is Addis Ababa. Direct flights to Addis Ababa are offered by Ethiopian Airlines (Star Alliance).
  • Flights from Chicago to Finland: Helsinki is the only destination in Finland with direct flights from Chicago. Direct flights to Helsinki are offered by Finnair (Oneworld).
  • Flights from Chicago to France: There is 1 destination in France that has a direct connection from Chicago, which is Paris. Non-stop flights to Paris are offered by Air France (SkyTeam), American Airlines (Oneworld), and United Airlines (Star Alliance).
  • Flights from Chicago to Germany: In Germany, there are 2 destinations from Chicago.
    • To Frankfurt and Munich, you can fly with Lufthansa (Star Alliance) and United Airlines (Star Alliance).
  • Flights from Chicago to Greece: Athens is the only destination in Greece with direct flights from Chicago. Direct flights to Athens are offered by American Airlines (Oneworld). This is a seasonal route that starts in August and ends in October.
  • Flights from Chicago to Guatemala: In Guatemala, the only destination that has a direct flight from Chicago is Guatemala City. Direct flights to Guatemala City are offered by American Airlines (Oneworld).
  • Flights from Chicago to Hong Kong: There is 1 destination in Hong Kong that has a direct connection from Chicago, which is Hong Kong. Direct flights to Hong Kong are offered by Cathay Pacific (Oneworld).
  • Flights from Chicago to Iceland: In Iceland, the only destination that has a direct flight from Chicago is Reykjavik (Keflavik). You can fly non-stop to Reykjavik (Keflavik) with Icelandair or United Airlines (Star Alliance).
  • Flights from Chicago to India: If you are looking for a direct flight from Chicago to India, there are 2 destinations to choose from.
  • Direct flights to Hyderabad are offered by Air India (Star Alliance): You can fly non-stop to New Delhi with Air India (Star Alliance) or United Airlines (Star Alliance).
  • Flights from Chicago to Ireland: Dublin is the only destination in Ireland with direct flights from Chicago. Non-stop flights to Dublin are offered by Aer Lingus, American Airlines (Oneworld), and United Airlines (Star Alliance).
  • Flights from Chicago to Israel: There is 1 destination in Israel that has a direct connection from Chicago, which is Tel Aviv. You can fly non-stop to Tel Aviv with EL AL or United Airlines (Star Alliance).
  • Flights from Chicago to Italy: Rome (Fiumicino) is the only destination in Italy with direct flights from Chicago. You can fly non-stop to Rome (Fiumicino) with American Airlines (Oneworld) or United Airlines (Star Alliance). This is a seasonal route that starts in September and ends in October.
  • Flights from Chicago to Jamaica: In Jamaica, the only destination that has a direct flight from Chicago is Montego Bay. You can fly non-stop to Montego Bay with American Airlines (Oneworld) or United Airlines (Star Alliance).
  • Flights from Chicago to Japan: There are 3 destinations in Japan that have non-stop flights from Chicago.
    • Direct flights to Osaka are offered by ANA (Star Alliance). This route has been announced recently and is not operational yet. It will start in July 2022.
    • Non-stop flights to Tokyo are offered by ANA (Star Alliance), Japan Airlines (Oneworld) and United Airlines (Star Alliance).
    • You can fly non-stop to Tokyo with ANA (Star Alliance) or Japan Airlines (Oneworld).
  • Flights from Chicago to Jordan: There is 1 destination in Jordan that has a direct connection from Chicago, which is Amman. Direct flights to Amman are offered by Royal Jordanian (Oneworld).
  • Flights from Chicago to Mexico: Mexico is well-connected to Chicago (ORD) with 12 destinations around the country that have direct flights from Chicago.
    • From Chicago to Cancún there are 5 airlines that have direct services, which are American Airlines (Oneworld), Frontier Airlines, Southwest Airlines, Spirit Airlines, and United Airlines (Star Alliance).
    • Non-stop flights to Cozumel are offered by American Airlines (Oneworld), Frontier Airlines, and United Airlines (Star Alliance).
    • Non-stop flights to Guadalajara are offered by AeroMexico (SkyTeam), VivaAerobus, and Volaris.
    • The only airline with direct flights to Ixtapa / Zihuatanejo is United Airlines (Star Alliance). This is a seasonal route that starts in December and ends in January.
  • Non-stop flights to León are offered by United Airlines (Star Alliance), VivaAerobus, and Volaris.
  • From Chicago to Mexico City there are 4 airlines that have direct services, which are Aeromexico (SkyTeam), United Airlines (Star Alliance), VivaAerobus, and Volaris.
    • You can fly non-stop to Monterrey with United Airlines (Star Alliance) or VivaAerobus.
    • You can fly non-stop to Morelia with VivaAerobus or Volaris.
    • You can fly non-stop to Puerto Vallarta with American Airlines (Oneworld) or United Airlines (Star Alliance).
    • The only airline with direct flights to Querétaro is Volaris.
    • You can fly non-stop to San José del Cabo with American Airlines (Oneworld) or United Airlines (Star Alliance).
    • You can fly non-stop from Chicago to Zacatecas with VivaAerobus. This is a seasonal route that starts in December and ends in January.
  • Netherlands – Flights from Chicago to the Netherlands: In the Netherlands, the only destination that has a direct flight from Chicago is Amsterdam. You can fly non-stop to Amsterdam with KLM (SkyTeam) or United Airlines (Star Alliance).
  • New Zealand – Flights from Chicago to New Zealand: Auckland is the only destination in New Zealand with direct flights from Chicago. Direct flights to Auckland are offered by Air New Zealand (Star Alliance). This route is not operational yet but will start in October.
  • Panama – Flights from Chicago to Panama: There is 1 destination in Panama that has a direct connection from Chicago, which is Panama City. Direct flights to Panama City are offered by Copa Airlines (Star Alliance).
  • Poland – Flights from Chicago to Poland: In Poland, there are 2 destinations from Chicago. To Krakow and Warsaw, you can fly with LOT (Star Alliance).
  • Portugal – Flights from Chicago to Portugal: Lisbon is the only destination in Portugal with direct flights from Chicago. Direct flights to Lisbon are offered by TAP Portugal (Star Alliance).
  • Puerto Rico – Flights from Chicago to Puerto Rico: In Puerto Rico, the only destination that has a direct flight from Chicago is San Juan. Non-stop flights to San Juan are offered by American Airlines (Oneworld), Frontier Airlines, and United Airlines (Star Alliance).
  • Qatar – Flights from Chicago to Qatar: There is 1 destination in Qatar that has a direct connection from Chicago, which is Doha. Direct flights to Doha are offered by Qatar Airways (Oneworld). Sint MaartenFlights from Chicago to Sint Maarten, In Sint Maarten, the only destination that has a direct flight from Chicago is Sint Maarten. Direct flights to Sint Maarten are offered by United Airlines (Star Alliance). This is a seasonal route that starts in November and ends in June.
  • South Korea – Flights from Chicago to South Korea: Seoul is the only destination in South Korea with direct flights from Chicago. Direct flights to Seoul are offered by Korean Air (SkyTeam).
  • Spain – Flights from Chicago to Spain: There are 2 destinations in Spain that have non-stop flights from Chicago. Direct flights to Barcelona are offered by American Airlines (Oneworld). This is a seasonal route that started in May and ends in June. The only airline with direct flights to Madrid is Iberia (Oneworld).
  • St. Lucia- Flights from Chicago to St. Lucia: There is 1 destination in St. Lucia that has a direct connection from Chicago, which is Saint Lucia. You can fly non-stop to Saint Lucia with American Airlines (Oneworld) or United Airlines (Star Alliance). This is a seasonal route that starts in November and ends in April.
  • Sweden – Flights from Chicago to Sweden: Stockholm (Arlanda) is the only destination in Sweden with direct flights from Chicago. Direct flights to Stockholm (Arlanda) are offered by SAS (Star Alliance). This route is not operational yet but will start in September.
  • Switzerland- Flights from Chicago to Switzerland: In Switzerland, the only destination that has a direct flight from Chicago is Zürich. You can fly non-stop to Zürich with Swiss (Star Alliance) or United Airlines (Star Alliance).
  • Taiwan – Flights from Chicago to Taiwan: There is 1 destination in Taiwan that has a direct connection from Chicago, which is Taipei. Direct flights to Taipei are offered by EVA Air (Star Alliance).
  • Turkey – Flights from Chicago to Turkey: In Turkey, the only destination that has a direct flight from Chicago is Istanbul. Direct flights to Istanbul are offered by Turkish Airlines (Star Alliance).
  • Turks & Caicos Islands- Flights from Chicago to Turks & Caicos Islands: Providenciales is the only destination in Turks & Caicos Islands with direct flights from Chicago. You can fly non-stop to Providenciales with American Airlines (Oneworld) or United Airlines (Star Alliance). This is a seasonal route that starts in November and ends in June.
  • U.S. Virgin Islands- Flights from Chicago to U.S. Virgin Islands: There is 1 destination in U.S. Virgin Islands that has a direct connection from Chicago, which is Saint Thomas. You can fly non-stop to Saint Thomas with American Airlines (Oneworld) or United Airlines (Star Alliance).
  • United Arab Emirates – Flights from Chicago to the United Arab Emirates: If you are looking for a direct flight from Chicago to the United Arab Emirates, there are 2 destinations to choose from.
  • Direct flights to Abu Dhabi are offered by Etihad Airways: The only airline with direct flights to Dubai is Emirates.
  • Flights from Chicago to the United Kingdom: In United Kingdom, there are 2 destinations from Chicago. Direct flights to Edinburgh are offered by United Airlines (Star Alliance). This is a seasonal route that started in May and ends in June. Non-stop flights to London Heathrow are offered by American Airlines (Oneworld), British Airways (Oneworld), and United Airlines (Star Alliance).

Best time to go Chicago

Spring (April to the end of May) and fall (September to the end of October) are both excellent times to visit Chicago, thanks to pleasant temperatures and fewer crowds.

Fall is especially nice, with daily temperatures averaging 60-70°F (15-21°C). You need to pack a sweater for this time of year, but tourist attractions are less crowded and hotel/hostel rooms are cheaper.

Summer (June-August) is the peak season in Chicago. It’s hot, with temperatures reaching the mid-80s°F (high 20s°C), and tourist crowds are at their highest. Although it’s nice to take advantage of the weather, keep in mind that prices increase for accommodations and vacancies are low. August can be rainy, so pack a light rain jacket.

Avoid visiting in winter unless you don’t mind some super cold days! The wind can be sharp during the winter months in Chicago, but if you want to do a lot of museum hopping or sightseeing indoors, you can save a lot of money on accommodations.

Chicago’s history is a big part of what makes it so unique. Taking a tour is definitely recommended if you want to learn about the city’s storied past, from the notorious gangsters to the famous buildings. Below are some of the most popular or unique tours on offer in the city.

Chicago Sightseeing Tours:

The four-hour Chicago Grand Half-Day Tour is the perfect way to be able to see and learn about the city’s most important landmark buildings and sights. The narrated coach tour takes a scenic route along the lake through Grant Park and past some of its most iconic attractions; drives down Chicago’s Magnificent Mile; and tours the South Side, where you can see President Obama’s former home.

For general sightseeing, the Hop-On Hop-Off Bus or Trolley Tour is the easiest and most convenient way to see the highlights of the city and to get oriented. For first-timers, this is a must. Get on and off at the sights that interest you, skip those that don’t, and learn a little history from this narrated tour.

If you are spending more than one day in the city, do this tour on day one to get the layout of the city and figure out where you might want to spend the rest of your time.

If you are visiting during the warmer months, consider taking a Segway Tour. These are small groups of just eight people and one guide. You will be given a short training session and then head off on a guided tour.

Chicago Special Interest Tours:

The Chicago Mob and Crime Tour is one of those unique tours that can only exist in certain cities, like Chicago. This tour takes you to sites associated with some of the city’s most notorious gangsters of the 20th century, including Al Capone and John Dillinger. Anyone who reads crime novels will love this tour.
During the summer months, check out the Chicago Architecture River Cruise. You don’t have to be an expert to appreciate the city’s fine buildings, and this 75-minute cruise is a great way to see and learn about Chicago’s architecture.

What are the best things to do in Chicago?

  • Millennium Park: The Chicago Loop’s art-filled urban park
    • Enter Chicago’s great “front lawn” – Millennium Park. The public space is where you can find some of the city’s most iconic scenery. Stroll through the blooming perennial Lurie Gardens, which are enclosed by a 15-foot-high hedge. Admire art installations along the tree-lined Chase Promenade, with different exhibitions held throughout the year. A must-see is Cloud Gate, fondly nicknamed “The Bean” for its shape. This giant sculpture features a smoothly polished mirror-like stainless steel surface, reflecting the skyscraper scene around it.
  • Navy Pier: A one-stop entertainment spot with an iconic Ferris wheel
    • The Navy Pier is a great spot for families to head to on Chicago’s Michigan lakefront. The pier juts out for over 3,000 ft into the lake and is filled with green spaces, shops, exhibitions, and restaurants. One of the pier’s main features that also dominates its skyline is the Centennial Wheel. This Ferris wheel is open daily, but the coolest experience must be during the Navy Pier Summer Fireworks that display in sync to music over Lake Michigan every Wednesday and Saturday.
  • Chicago Riverwalk: For a sightseeing trip through the heart of the city
    • Before the flows of the Chicago River meet Lake Michigan, it runs through most of The Loop. One of the best ways to see the city from up close is the Chicago Riverwalk, a gentrified waterfront path through downtown, along the river’s south bank. Start your walks from Lake Shore Drive and up to Lake Street. Along the way, you have plenty of restaurants, park gardens, and bridges, where you can pause and take in the high-rise city views.
  • Adler Planetarium: Travel through space, then back to Earth for Chicago’s sweeping skyline
    • Founded in 1930, Adler Planetarium is a monumental science facility occupying the north-eastern tip of Chicago’s Northerly Island. It has a vintage charm with its prominent planetarium dome and Art Deco exterior embellished with bronze zodiac reliefs. From inside the dome, you can travel through the universe through the Grainger Sky Theater’s digital projection. Scenic offerings outside include the 12th Street Beach, the boat docks of Burnham Harbor, and ultimately, the Skyline Walk from where you can take in the best views of Chicago.
  • Magnificent Mile: Chicago’s bustling commercial heart
    • If you’re looking for the most luxurious shopping scene in Chicago, head down to the Magnificent Mile. It’s part of North Michigan Avenue, where you can find a series of upscale shops, hip dining spots, and some of Chicago’s finest big-brand hotels, such as the Four Seasons, Ritz-Carlton, The Conrad, and Park Hyatt. Grand malls here include Nordstrom, and Water Tower Place, which houses a Macy’s. Come in the summer and you can experience the Gardens of The Magnificent Mile festival, where its blooming planters are sometimes graced with designer fashion.
  • Skydeck Chicago: Enjoy thrilling city views from up high
    • This feature lets you literally stand on the edge of the 103rd-floor of one of the world’s tallest skyscrapers, at over 1,300 feet high, overlooking the Chicago cityscape. You can get a good view from the Skydeck observatory, but the real highlight is the appropriately named ‘The Ledge’. You step into either of the 2 glass boxes which extend out, with your feet seemingly hovering over the dizzying heights below. Another similar sensation that lets you experience the heights over the city is 360 Chicago, a 94th-floor observatory at the John Hancock Building. Rather than stationery, its lookout is a tilting glass enclosure for added thrills.
  • Try Chicago-style pizza: The city’s signature deep-dish pie
    • When in Chicago, don’t miss out on trying the city’s signature pizza. They don’t do them thin-crusted here. Rather, Chicago-style pizza is a deep-dish preparation, using a deep pan with added toppings and cheese. One of the longstanding pizza houses where you can order the original pizza is Pizzeria Uno on East Ohio Street. They have a second branch, Pizzeria Due, on North Wabash Avenue. You can usually choose from cheese, sausage, pepperoni, or the Original Numero Uno, all of which come in 10-inch deep-dish sizes.
  • Chicago Theatre: Evenings out in Chicago for music or comedic acts
    • A high-rise Chicago landmark that features French Baroque architecture 7 stories tall, the Chicago Theatre is where you can watch the latest rock bands, Broadway musicals, as well as comedic acts perform. These range from hit TV musical series brought to life on-stage such as Bring It! Live, to performances of rock to synth-pop bands, and hilarious nights with wisecracking acts such as Russel Peters. Ticket prices vary per event and your chosen seating level, but start from around $40.

The Chicago’s Attractions

  1. Cloud Gate (The Bean): If you have seen photos of Chicago on Instagram or Facebook, chances are you have seen photos of Cloud Gate (which most people call The Bean), the famous mirrored sculpture in Millennium Park.
    Millennium Park is usually crowded (especially in the summer and on weekends) so to avoid the crowds visit early in the morning or later in the day. If you are visiting Chicago with children, you might want to also visit Maggie Daley Park, a large public park connected to Millennium Park that has play areas for kids of various ages.
  2. Navy Pier: Some locals consider Navy Pier a bit of a tourist trap, but it is a not to missed attraction if you are visiting Chicago with kids. Navy Pier is full of fun things to do including a large Ferris wheel, restaurants, shops, the Chicago Children’s Museum, and the Chicago Shakespeare Theater. Navy Pier is also the starting point for various sightseeing cruises and boat rides. Navy Pier is free although you have to pay for the attractions and restaurants.
  3. Great Museums: Chicago has many great museums which are well known and worth visiting. Depending on how much you enjoy museums, you might want to spend some time in one or more of them when visiting Chicago.
    • To save money on entrance fees and skip long lines if you are visiting several museums, consider purchasing a Chicago CityPASS. Take advantage of free museum days. Some of the best Chicago museums offer free admission on the first weekend of every month to Bank of America credit or debit cardholders under the Bank of America Museums on Us program.
  4. Architecture: Chicago has amazing architecture and the best way to see it is by taking an architecture river cruise. Because the water sometimes freezes in the winter, river cruises only operate part of the year.
  5. Chicago Riverwalk: The Chicago Riverwalk, a pedestrian promenade along the river, is another must-see Chicago attraction especially in the summer. The Riverwalk is one of the best spots in Chicago for people watching and it has restaurants, bars, and other spots to sit along the way.
  6. Skyscrapers: Chicago is famous for its tall skyscrapers especially the Willis Tower (formerly known as the Sears Tower and what locals still call it) which used to be the tallest building in the world from 1974 until 1998. One of the best ways to see Chicago is to check out the view from one of its two tallest buildings. Chicago has two famous skyscrapers with observation decks:
  7. Famous Chicago Food: Chicago is one of the best cities in the world for food lovers! Although Chicago is famous for certain dishes – there is so much more great food in Chicago. Don’t limit yourself to just these iconic Chicago dishes, but you should definitely try these once! If you don’t have plans to visit Chicago soon, you can order some of these dishes online and enjoy a home.
    • If your time in Chicago is short, consider a food tour:
  8. Chicago-style hot dog: A Chicago-style hot dog or Chicago dog is one of the two foods that Chicago is most famous for. The classic version of the Chicago dog is an all-beef hot dog served on a poppy seed bun and topped with yellow mustard, pickle, relish, sliced tomato, onions, sport peppers, and celery salt. Ketchup is famously not allowed.
  9. Italian beef sandwich: Although not as well-known as deep-dish pizza and Chicago-style hot dogs, Italian beef is another dish Chicago is famous for. Al’s Italian Beef is the best and most famous place in Chicago to try an Italian beef sandwich. Another good spot is Portillos if you are there for a Chicago hot dog.
  10. Art Institute of Chicago: The Art Institute of Chicago is a world-class museum with hundreds of thousands of artworks. The diverse collection spans thousands of years and includes pieces from a variety of media including painting, prints, photography, sculpture, decorative arts, textiles, architectural drawings, and more.
  11. Museum of Science and Industry: At the north end of Jackson Park is the Museum of Science and Industry, founded in 1933, and arguably the most impressive museum in Chicago. It is devoted to the application of natural laws in technological and industrial development.
  12. 360 Chicago: Located in the John Hancock Center office building, 360 Chicago is an observation deck on the 94th floor of the John Hancock Building, easy to recognize by its dark metallic-looking exterior and cross-braced steel design, which runs up the outside of the building. The large glass-walled observation deck has views that look out over Chicago’s skyline and beyond.
  13. More adventurous tourists will love the deck’s newest feature, “Tilt,” which gives visitors a unique view from more than 1,000 feet above the Magnificent Mile as they are tipped outward at an angle to look straight down from the glass enclosure.
  14. Take a Tour or See a Game at Wrigley Field: Wrigley Field, home to the Chicago Cubs, was built in 1914 and is the second-oldest Major League Baseball Park in the US, second only to Fenway Park in Boston. The Park has seen some legendary moments in baseball history, including the 1917 no-hitter pitching duel between the Cubs’ Jim Vaughn and the Reds’ Fred Toney, and Babe Ruth’s “called shot” during game three of the 1932 World Series.
  15. Lincoln Park: Lincoln Park is a six-mile stretch of green space along the edge of Lake Michigan, and Chicago’s biggest park. This popular park is home to the lovely Lincoln Park Conservatory and the Lincoln Park Zoo, one of the oldest zoos in the country. Also located here is the Peggy Notebaert Nature Museum, and the Chicago History Museum.
  16. Shedd Aquarium: If Lake Michigan has you wondering what sort of aquatic life exists just offshore from downtown Chicago, swing by the Shedd Aquarium. Inside are exhibits that cover aquatic regions of the world, from the Arctic to the Caribbean.
  17. Lincoln Park Zoo: Another fun thing for families to do in Chicago is a trip to the Lincoln Park Zoo. The zoo is home to over 200 species from around the world. Sixteen different exhibits showcase the wonderful animals that we share this world with. Some of the most entertaining animals include penguins, otters, and seals. For a truly fascinating experience, stop by the Regenstein Center for African Apes.
  18. The Rookery Building: The Rookery Building was designed by architects Daniel Burnham and John Root in 1888, but the interior lobby and patio were remodeled by Frank Lloyd Wright in 1907. This 12-story building has a Roman Revival and Queen Anne-style façade, but it is the central light court and the ornamental ironwork of the elegant staircases that are the true gem of the building.

Chicago Travel Guide: Money-Saving Tips

Chicago is an expensive city, especially when it comes to attractions and accommodation. But, like any major city, there are always pockets of affordability if you know where to look. Here are some ways to save money in Chicago:

  • Get the Chicago City Pass – This pass allows you to over 50% off admission at a number of attractions. A 5-Choice Explorer pass is $124 USD and gets you entrance into five different attractions like the Shedd Aquarium, the Skydeck, the Field Museum, and the Art Institute of Chicago. There are options ranging from 2-Choice to 7-Choice and also an all-inclusive pass.
  • Redeem hotel points – Be sure to sign up for hotel credit cards before you go and use those points when you travel. Be aware that most hotels charge parking fees if you have a car, and adjust your budget accordingly.
  • Couchsurf – Couchsurfing is the best way to save money in Chicago. You’ll not only get a free place to stay but you get to connect with a local who can share their insider tips. It’s perfect for budget travelers who want to make connections.
  • Go on a free walking tour – This is a great way to learn the history behind the places you are seeing and to avoid missing any must-see stops. Free Chicago Walking Tours has several interesting walking tours that can show you the main sights. Just be sure to tip your guide!
  • Save money on rideshares – Uber, Via, and Lyft are way cheaper than taxis and are the best way to get around a city if you don’t want to take a bus or pay for a taxi.
  • Bring a water bottle – The tap water here is safe to drink so bring a reusable water bottle to save money and reduce your plastic use. LifeStraw is my go-to brand as their bottles have built-in filters to ensure your water is always clean and safe.
 
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