Cheap Flight Deals to Chicago IL from C$196

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How to find cheap flights to Chicago?

The cheapest prices found with in the last 7 days for return flights were C$75 and C$196 for one-way flights to Chicago for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
DFWChicago13 Oct. - 17 Oct.C$75
LAXChicago14 Oct. - 17 Oct.C$93
LGAChicago12 Oct. - 17 Oct.C$119
ATLChicago24 Sep. - 26 Sep.C$133
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
EWRChicago18 Sep. - 20 Sep.C$161
*Prices include taxes and fees

Your guide to flights to Chicago, IL

Porter Airlines fly to Chicago, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Chicago IL currently costs between C$75 and C$337. Prices vary, but for the best fares, travel in October when prices are at their lowest.  

Top tips for finding cheap flights to Chicago  

The cheapest flight for a round trip to Chicago is currently C$75. When you search for flights to Chicago, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Chicago for nearby days.  The cheapest month to travel to Chicago is October from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Chicago 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Chicago with Travelocity 

We have top deals on plane tickets even for last minute flights to Chicago, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Chicago for less. 

Flights to Chicago: Customer Reviews

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Chicago

Freehand Chicago

Freehand Chicago

3.5 out of 5
19 East Ohio Street, Chicago, IL
The price is C$150 per night from Sep 20 to Sep 20
Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...
4/5Very Good! (21 reviews)
"Comfortable, laid back, cozy atmosphere."

Reviewed on 8 May 2021

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
The price is C$150 per night from Sep 26 to Sep 26
Located in The Loop, this hotel is steps from Columbia College Chicago, Grant Park, and State Street. Art Institute of Chicago and Buckingham Fountain are also ...
3.6/5Good! (40 reviews)
"The room looked a little run down, very basic."

Reviewed on 12 Aug. 2021

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is C$54 per night from Oct 5 to Oct 5
Situated in Elk Grove Village, this motel is 2.1 mi (3.3 km) from Lake Park and 2.8 mi (4.6 km) from Allstate Arena. Apache Park is 2.9 mi (4.7 km) away.
3.4/5 (26 reviews)
"The hardest bed I ever slept on. Concrete is harder, A little."

Reviewed on 21 Dec. 2019

Motel 6 Elk Grove Village, IL - O'Hare
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Ohio House Motel

Ohio House Motel

2.5 out of 5
600 North LaSalle Street, Chicago, IL
The price is C$143 per night from Sep 20 to Sep 20
Located in River North, this motel is within a 15-minute walk of Merchandise Mart and Wrigley Building. John Hancock Center and Navy Pier are also within 2 mi ...
4/5Very Good! (18 reviews)
"Great location. Nice rooms. Parking very handy. Management and staff worked with us on some special needs. Very pleased."

Reviewed on 5 Apr. 2021

Ohio House Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Our Top Chicago hotel with Airport Shuttles

Super 8 by Wyndham Chicago O'Hare Airport

Super 8 by Wyndham Chicago O'Hare Airport

2.5 out of 5
2951 Touhy Ave, Elk Grove Village, IL
The price is C$95 per night from Oct 3 to Oct 3
Situated near the airport, this hotel is 2.8 mi (4.4 km) from Allstate Arena and within 9 mi (15 km) of Rivers Casino and Pirates Cove Childrens Theme Park. ...
3.7/5Good! (19 reviews)
"Kids loved the pool."

Reviewed on 17 Aug. 2021

Super 8 by Wyndham Chicago O'Hare Airport
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
777 East Grand Avenue, Bensenville, IL
The price is C$106 per night from Sep 20 to Sep 20
Situated near the airport, this hotel is 1.6 mi (2.5 km) from Edge Ice Arena and within 6 mi (10 km) of Rosemont Theatre and Fashion Outlets of Chicago. Donald ...
3.4/5Good! (53 reviews)
"This was a decent place to spend the night. The room was big enough but not huge, and 4 of us slept comfortably. The check-in process was quick and the help was friendly. Breakfast was ok, but missed having some fruit or beverage options that included fruit."

Reviewed on 13 Aug. 2021

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Hampton Inn Chicago - O'Hare

Hampton Inn Chicago - O'Hare

2.5 out of 5
3939 N Mannheim Rd, Schiller Park, IL
The price is C$141 per night from Oct 15 to Oct 15
Situated near the airport, this hotel is within 3 mi (5 km) of Rosemont Theatre, Fashion Outlets of Chicago, and Donald E. Stephens Convention Center. Parkway ...
4.5/5Wonderful! (38 reviews)
"Great service and staff!!"

Reviewed on 6 Sep. 2021

Hampton Inn Chicago - O'Hare
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Holiday Inn O'Hare, an IHG Hotel

Holiday Inn O'Hare, an IHG Hotel

3 out of 5
5615 North Cumberland Avenue, Chicago, IL
The price is C$153 per night from Sep 26 to Sep 26
Located in O'Hare, this hotel is within 3 mi (5 km) of Rivers Casino, Donald E. Stephens Convention Center, and Rosemont Theatre. Parkway Bank Park Entertainment ...
3.7/5Good! (19 reviews)
"nice facility, not enough towels/cloths in room and was not available when requested; would return"

Reviewed on 6 Apr. 2021

Holiday Inn O'Hare, an IHG Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Hotels in Chicago

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
401 N Wabash Ave, Chicago, IL
The price is C$454 per night from Oct 17 to Oct 17
This family-friendly Chicago hotel is located near the beach, within a 10-minute walk of State Street, House of Blues Chicago, and Chicago Theatre. Chicago Riverwalk ...
4.9/5Exceptional! (18 reviews)
"Travelocity asks what are the negatives; well, the only negative is that I cannot come up with anything negative, which is pretty much a first. In short: picking Trump Int’l was a very good choice"

Reviewed on 22 Aug. 2020

Trump International Hotel & Tower Chicago
The Langham, Chicago

The Langham, Chicago

5 out of 5
330 North Wabash Avenue, Chicago, IL
The price is C$567 per night from Oct 14 to Oct 14
This family-friendly Chicago hotel is located in the entertainment district, within a 15-minute walk of Michigan Avenue, Millennium Park, and Art Institute of ...
5/5Exceptional! (7 reviews)
"Excellent service. The hotel is beautiful. Would definitely stay here again."

Reviewed on 6 Jun. 2021

The Langham, Chicago
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
108 East Superior Street, Chicago, IL
The price is C$663 per night from Sep 26 to Sep 26
This family-friendly Chicago hotel is located in the historical district, steps from Chicago Water Tower, Michigan Avenue, and Museum of Contemporary Art. Water ...
5/5Exceptional! (5 reviews)
"Our room was ready earlier than expected and everyone was helpful and amazingly friendly. This is a must stay when in Chicago and number one on our list. Our kids loved the place as well."

Reviewed on 28 Mar. 2019

The Peninsula Chicago
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The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
521 North Rush Street, Chicago, IL
The price is C$396 per night from Oct 17 to Oct 17
Located in River North, this luxury hotel is steps from Tribune Tower and Michigan Avenue. House of Blues Chicago and Water Tower Place are also within 10 minutes. ...
4.3/5Excellent! (12 reviews)
"Top notch hotel in the heart of downtown Chicago right on Michigan Ave. Very comfortable lobby and common area."

Reviewed on 2 Jan. 2020

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Chicago

Embassy Suites Chicago Downtown Magnificent Mile

Embassy Suites Chicago Downtown Magnificent Mile

4 out of 5
511 North Columbus Drive, Chicago, IL
The price is C$213 per night from Sep 20 to Sep 20
Located in Near North Side, this hotel is within a 5-minute walk of Chicago Riverwalk and Michigan Avenue. Northwestern Memorial Hospital and State Street are ...
4/5Very Good! (55 reviews)
"It was centrally located to access of all transportation types."

Reviewed on 17 Jul. 2021

Embassy Suites Chicago Downtown Magnificent Mile
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
The price is C$264 per night from Sep 26 to Sep 26
Located in The Loop, this spa hotel is within a 5-minute walk of Art Institute of Chicago and Millennium Park. Chicago Theatre and Willis Tower are also within ...
4.3/5Excellent! (85 reviews)
"QUE CIERRAN LA PISCINA DEBERIA ESTAR ABIERTO 24 HORAS"

Reviewed on 30 Jul. 2021

Palmer House a Hilton Hotel
Embassy Suites Chicago Downtown

Embassy Suites Chicago Downtown

4 out of 5
600 N State St, Chicago, IL
The price is C$201 per night from Sep 19 to Sep 19
Located in River North, this hotel is steps from Chinese Consulate and State Street. House of Blues Chicago and Chicago Riverwalk are also within 10 minutes. ...
4.3/5Excellent! (37 reviews)
"Great location! Easy walking distance to the Riverwalk, Magnificent Mile, dining, and transportation."

Reviewed on 1 Sep. 2021

Embassy Suites Chicago Downtown
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Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
The price is C$301 per night from Sep 28 to Sep 28
Located in The Loop, this eco-friendly hotel is steps from Chicago Riverwalk and Michigan Avenue Bridge. Grant Park and Chicago Theatre are also within 10 minutes. ...
4.3/5Excellent! (93 reviews)
"Staff were friendly Hotel was quiet. Handicapped door was broken in accessible room. Clean towels only after four days NO Concierge!"

Reviewed on 14 Sep. 2021

Hyatt Regency Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Best Chicago Flight and Hotel Packages

Chicago flight + hotel packages - economy flights

The Langham, Chicago
Sheraton Grand Chicago
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FAQs about Chicago Flights

Can I catch a flight to Chicago at the moment?

For the latest complete info regarding passengers on flights bound for Chicago, check out our Covid-19 Travel Advisor. Everything you need to know about current travel restrictions and quarantine requirements is located here in one convenient place.

Which airlines fly to Chicago?

When it comes to airlines that offer flights to Chicago, you're flush with choice. There are 20 companies that operate in this major city. Book your favorite seat on one of these leading carriers:

  • United Airlines
  • American Airlines
  • Southwest Airlines
If I am not able to travel due to COVID-19, can I change my booking to a later date?

For more info about changing your flight to Chicago, please visit our Customer Service Portal.

What airport is best to fly into Chicago?

When looking up flights in and out of Chicago, explore all available options. With a few airports near the city, the price of your tickets may differ depending on which one you select. Here are the most popular of them:

  • O'Hare Airport – 26 kilometers from downtown
  • Chicago, IL Airport (MDW-Midway Intl.) – 14 kilometers from downtown
  • Joliet Park District Airport (JOT) – 60 kilometers from downtown
Where to stay in Chicago

Researching a trip to Chicago? Let Travelocity help you create some extraordinary new memories. You'll find 4,256 instantly bookable accommodations to choose from on our site.

Indulge in a bit of luxury at the Palmer House a Hilton Hotel or the Silversmith Hotel Chicago Downtown. After all, it's not every day you take a vacation! However, if you don't think you'll spend much time in your suite, how about a cheaper option like the HI Chicago or the Travelodge by Wyndham Downtown Chicago?

Fancy staying close to McCormick Place? Now's the time! Both the Hyatt Regency McCormick Place and the Marriott Marquis Chicago are comfortable places and are just a walk away.

Places to visit in Chicago

With so many unmissable attractions in Chicago, you might just have to let the boss know that you need an extra week off. Begin with Art Institute of Chicago, and Millennium Park. You'd also be nuts to miss out on seeing Skydeck Ledge, and Willis Tower.

Experience the fabulous flavors of this lively metropolis by enjoying places like Chicago Cultural Center, and Buckingham Fountain. If you want more options, Merchandise Mart, and Wrigley Building are worth a look too.

If you are a fan of theater, be sure to take in a play at Chicago Theatre. Like some more options? Many of the best tourist attractions are situated in Chicago Riverwalk area. But that's not all. Venture to Water Tower Place and look up. You'll be thrilled by how grand this building is.

How to get through airport security fast when traveling to Chicago

Make your flight to Chicago a little bit easier by following these helpful tips and pointers:

  • Security staff will expect to see your travel ID and boarding pass as part of their checks. Store them in an accessible place, so they're ready for inspection.
  • Wallets, belts and mobile phones should be put in a tray for X-raying. If you pass through the body scanner with these items, you'll be turned back and instructed to remove them.
  • Electronic items such as tablets, laptops and phones are always sent through the X-ray machine separately. Make sure they're easily accessible.
  • When you get to the security checkpoint, you'll be asked to place all creams, gels and liquids in a separate tray for scanning. Make sure they're all stored in containers smaller than 3.4 ounces (161 milliliters) and sealed in a clear zip-lock bag.
  • Untie your shoelaces before approaching the body scanner. Depending on what sort of shoes you're wearing, security may instruct you to remove them.
  • Pocketknives and corkscrews are not permitted on board the aircraft. Pack them in your checked luggage to avoid forfeiting them at the security checkpoint.

Flights To Chicago

Each time you visit Chi-Town, you’ll fall in love anew. Even if you’ve stood in front of the famous metallic bean and stood along the Navy Pier, you won’t be left wanting for original ways to spend your time. As Mark Twain posited, “She is novelty, for she is never the same Chicago you saw when you passed through the last time.” The modern city on the shores of Lake Michigan is always evolving and will never fail to enchant you. Between the exciting sports culture and buildings that hearken back to a time when Frank Sinatra and Al Capone ran the scene, Chicago always impresses.

Flights to Chicago depart from tons of destinations; just sit back, start dreaming of deep-dish pizza, and before you know it you’ll be touching down in the Windy City. Book your airfare on Travelocity today, and you’ll save enough cash to afford all the famous frankfurters you want.

Transportation from Chicago Airports

Chicago flights land at one of the two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW). Getting to downtown Chicago from ORD is a breeze when you take the Blue line train, which is part of the Chicago Transit Authority train system. From MDW, jump on the Orange line train.

If you’re not staying downtown, buses are available to most parts of the city from both airports. When a private ride is more your style, hail a taxi outside the baggage claim area. Many hotels also have shuttle buses that will take you to and from the airport. But if independence is more your style, there are many rental car companies located within the airport if you need your own wheels; book your ride when you purchase your airfare to Chicago and your vacation is set.

Hotels Near ORD and MDW

A savvy traveler such as yourself is sure to purchase one of our top flight deals to Chicago. Not only will you travel on one of the most affordable and convenient flights, but you’re wise enough to book a Chicago hotel befitting of your fine taste:

  • The Palmer House Hilton: This hotel bills itself as hip and historic, and one step inside the lobby lets you know the description is spot on. Opulent ceilings and marble accents remind you of an era when dinner was always a formal affair, while the rooms are adorned in bright furniture and clean modern lines.
  • Wyndham Grand Chicago Riverfront: From the cocktails served fireside at Hoyt’s Patio to in-room massages, this downtown hotel is designed to pamper. Get a room with a view and overlook the Windy City from the moment you wake up, and let the concierge help you book excursions to Chicago attractions.
  • Hyatt Regency Chicago: This four-diamond hotel is connected to the Illinois Center downtown, right in the heart of the city. You’ll be just a short and leisurely walk from the Magnificent Mile and Grant Park.
  • Congress Plaza Hotel: Legendary hotels are just your style, so this Grant Park hotel has your name on it. Enjoy a view of Lake Michigan from your room, and revel in the property’s storied history, which dates back to 1893.

Things to Do in Chicago

The Windy City is known for its pizza and beloved sports teams, but the Midwest powerhouse packs a cultural punch and can impress even seasoned world travelers. Begin your exploration with an investigation of Millennium Park, and then get a taste of Chi-Town’s creative offerings at the Art Institute of Chicago. From the observation deck of the Willis Tower, you can spot your favorite attractions and plot your route of the city. Like the savvy tourist you are, you booked cheap plane tickets to Chicago. Go ahead, buy entrance to the Lincoln Park Conservatory and Brookfield Zoo.

Use Travelocity to search through the flight options to the Windy City. Once you find one of the cheapest flights to Chicago and buy your tickets, there is nothing left to do but start dreaming of mozzarella and pack your bags. Chi-Town is waiting to welcome you with open arms and delight you with its Midwest charms.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.