Cheap Flight Deals to Chicago IL from CA $99

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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 CA $196 and CA $99 for one-way flights to Chicago for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
DFWChicagoAugust 15 to August 18CA $239
JFKChicagoJuly 12 to July 13CA $256
LAXChicagoAugust 22 to August 24CA $337
LAXChicagoSeptember 12 to September 18CA $594
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
ATLChicagoJuly 9 to July 10CA $324
EWRChicagoJuly 9 to July 10CA $435
*Prices include taxes and fees

Your guide to flights to Chicago, IL

Swoop, Spirit Airlines fly to Chicago, so use Travelocity to search, find, and compare some truly tempting deals from the 4 airlines—that way you can be sure you’ve found the best deal for you. A flight to Chicago IL currently costs between CA $196 and CA $594. Prices vary, but for the best fares, travel in August 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 CA $196. 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 September 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. 

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, 60611
The price is CA $163 per night from Jul 6 to Jul 7
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
4.1/5 Very Good! (16 reviews)
"Unique hotel and cozy rooms"

Reviewed on 1 Jan. 2022

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL, 60605
The price is CA $203 per night from Aug 1 to Aug 2
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and onsite parking. Our guests praise the breakfast and the restaurant in our reviews. ...
3.5/5 Good! (44 reviews)
"Amazing friendly staff and felt very safe!"

Reviewed on 9 Apr. 2022

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, 60007
The price is CA $71 per night from Aug 1 to Aug 2
Stay at this business-friendly motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
3.6/5 Good! (25 reviews)
"The staff was cooperative. Everything was as described."

Reviewed on 12 Mar. 2022

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, 60654
The price is CA $209 per night from Jul 5 to Jul 6
Stay at this business-friendly motel in Chicago. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the clean rooms in our ...
4/5 Very Good! (18 reviews)
"It was very cold in my room I called downstairs asking where was the heat they said it was in the office I asked them to turn it up they said okay but they never did it was cold cold"

Reviewed on 8 May 2022

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, 60007
The price is CA $104 per night from Jul 10 to Jul 11
Stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
3.9/5 Very Good! (22 reviews)
"It was a good experience staying at the hotel"

Reviewed on 6 Jan. 2022

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, 60106
The price is CA $144 per night from Jul 11 to Jul 12
Stay at this 3-star business-friendly hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
3.3/5 (48 reviews)
"Great hotel! It was comfy and clean. The morning breakfast was very tasty."

Reviewed on 3 Apr. 2022

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, 60176
The price is CA $197 per night from Jul 25 to Jul 26
Stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
4.6/5 Wonderful! (39 reviews)
"After travel delays all day coming to the hotel around midnight was the closest thing to coming home before my actual flight home the next day. Your staff from the front desk to housekeeping staff were top notch! The shuttle drivers were fantastic! Thank you for making my trip easy and ..."

Reviewed on 14 Mar. 2022

Hampton Inn Chicago - O'Hare
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You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Holiday Inn O'Hare, an IHG Hotel

Holiday Inn O'Hare, an IHG Hotel

3 out of 5
5615 North Cumberland Avenue, Chicago, IL, 60631
The price is CA $174 per night from Aug 1 to Aug 2
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the convenient ...
3.6/5 Good! (22 reviews)
"I love the Holiday Inn on cumberland because it is close to the freeway and it has great parking , the staff is always the best and me and my famy love everything about it"

Reviewed on 21 Dec. 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, 60611
The price is CA $547 per night from Aug 1 to Aug 2
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the breakfast and the helpful staff in our ...
4.8/5 Exceptional! (18 reviews)
"Perfect location; service was impeccable"

Reviewed on 30 Apr. 2022

Trump International Hotel & Tower Chicago
The Langham, Chicago

The Langham, Chicago

5 out of 5
330 North Wabash Avenue, Chicago, IL, 60611
The price is CA $673 per night from Aug 1 to Aug 2
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the helpful staff and the comfy rooms in our ...
5/5 Exceptional! (8 reviews)
"Everyone was very friendly and helpful. The room was wonderful. I loved that the lighting was labeled and that there was an abundance of hooks. Sounds insignificant but made settling in easy. The people at the entrance were especially helpful and friendly."

Reviewed on 27 Sep. 2021

The Langham, Chicago
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
108 East Superior Street, Chicago, IL, 60611
The price is CA $806 per night from Jul 5 to Jul 6
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and a rooftop terrace. Our guests praise the pool and the helpful staff in ...
5/5 Exceptional! (6 reviews)
"Very good customer service, thanks,"

Reviewed on 25 Apr. 2022

The Peninsula Chicago
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You could be seeing lower prices

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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, 60611
The price is CA $515 per night from Jul 5 to Jul 6
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and a rooftop terrace. Our guests praise the bar and the helpful staff in our ...
4.3/5 Excellent! (11 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, 60611
The price is CA $257 per night from Jul 5 to Jul 6
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, WiFi, and room service. Our guests praise the breakfast and the helpful staff in ...
4/5 Very Good! (50 reviews)
"Great customer service! Great snacks included in room as well as breakfast!!"

Reviewed on 21 Jun. 2022

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, 60603
The price is CA $302 per night from Jul 5 to Jul 6
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the helpful staff in our reviews. Popular attractions ...
4.4/5 Excellent! (51 reviews)
"The history features were nice"

Reviewed on 31 May 2022

Palmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL, 60654
The price is CA $240 per night from Aug 1 to Aug 2
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, WiFi, and room service. Our guests praise the breakfast and the helpful staff in ...
4.4/5 Wonderful! (27 reviews)
"The bed in 401 could’ve been a little better shape."

Reviewed on 20 Jun. 2022

Embassy Suites by Hilton Chicago Downtown River North
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You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL, 60601
The price is CA $308 per night from Jul 6 to Jul 7
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
4.3/5 Excellent! (90 reviews)
"The property is in a great location."

Reviewed on 30 May 2022

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

Kimpton Gray Hotel, an IHG Hotel
W Chicago - City Center
JW Marriott Chicago
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Chicago flight + hotel packages - first class flights

Chicago Athletic Association, part of Hyatt
Hyatt Centric Chicago Magnificent Mile
Swissotel - Chicago
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Need a car after flight to Chicago?

Frequently asked questions

How to find cheap flights

What is the best day to buy a plane ticket?

Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you’re looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you’re browsing flight deals.


What are the cheapest days to fly?

Frequent travellers may already know this, earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.


How far in advance can you book a flight?

Here’s the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.

*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

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.