Cheap Flight Deals to Chicago IL from CA $64

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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 $198 and CA $64 for one-way flights to Chicago for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
BWIChicagoApril 27 to May 1CA $198
IADChicagoMarch 27 to March 31CA $775
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
DCAChicagoMarch 23 to April 3CA $497
*Prices include taxes and fees

Your guide to flights to Chicago, IL

Spirit Airlines, United 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 $198 and CA $775. Prices vary, but for the best fares, travel in April 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 $198. 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 April 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

4 out of 5
19 East Ohio Street, Chicago, IL
The price is CA $79 per night from Mar. 31 to Apr. 1
CA $79
per night
Mar. 31 - Apr. 1
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.6/10 Good! (1,005 reviews)
"Good choice for the price. The location is surrounded by lots of other hotels, and is close to downtown attractions."

Reviewed on 16 Mar. 2024

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 CA $112 per night from Mar. 31 to Apr. 1
CA $112
per night
Mar. 31 - Apr. 1
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.2/10 (1,565 reviews)
"OK"

Reviewed on 15 Mar. 2024

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 CA $81 per night from Mar. 26 to Mar. 27
CA $81
per night
Mar. 26 - Mar. 27
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (1,143 reviews)
"Nice and excellent area for airport travelers"

Reviewed on 15 Mar. 2024

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

Ohio House Motel

2.5 out of 5
600 N La Salle Drive, Chicago, IL
The price is CA $111 per night from Mar. 21 to Mar. 22
CA $111
per night
Mar. 21 - Mar. 22
Stay at this motel in Chicago. Enjoy free WiFi, onsite parking, and a 24-hour front desk. Our guests praise the helpful staff and the convenient parking in our ...
8.8/10 Excellent! (1,003 reviews)
"The rooms were nice and clean but parking was inconvenient. And to put down a deposit is more than the rate of the room."

Reviewed on 11 Mar. 2024

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 CA $97 per night from Mar. 24 to Mar. 25
CA $97
per night
Mar. 24 - Mar. 25
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 ...
7.8/10 Good! (1,003 reviews)
Clean, on the highway, large room
"Just got here😃"

Reviewed on 16 Mar. 2024

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 CA $102 per night from Mar. 24 to Mar. 25
CA $102
per night
Mar. 24 - Mar. 25
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.4/10 (1,004 reviews)
"."

Reviewed on 11 Mar. 2024

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

Hampton Inn Chicago-O'Hare International Airport

2.5 out of 5
3939 N Mannheim Rd, Schiller Park, IL
The price is CA $120 per night from Mar. 24 to Mar. 25
CA $120
per night
Mar. 24 - Mar. 25
Stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,250 reviews)
"Clean rooms & very nice staff"

Reviewed on 17 Mar. 2024

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

Holiday Inn Chicago O'Hare Area, an IHG Hotel

3 out of 5
5615 North Cumberland Avenue, Chicago, IL
The price is CA $128 per night from Apr. 1 to Apr. 2
CA $128
per night
Apr. 1 - Apr. 2
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast. Our guests praise the breakfast and the helpful staff in ...
7.4/10 Good! (1,000 reviews)
"Does everything it’s supposed to do."

Reviewed on 10 Mar. 2024

Holiday Inn Chicago O'Hare Area, 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 CA $472 per night from Mar. 24 to Mar. 25
CA $472
per night
Mar. 24 - Mar. 25
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the restaurant and the helpful staff in our ...
9.2/10 Wonderful! (1,111 reviews)
"Excellent location, amazing hotel."

Reviewed on 17 Mar. 2024

Trump International Hotel & Tower Chicago
The Langham, Chicago

The Langham, Chicago

5 out of 5
330 North Wabash Avenue, Chicago, IL
The price is CA $501 per night from Apr. 14 to Apr. 15
CA $501
per night
Apr. 14 - Apr. 15
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the restaurant and the helpful staff in our ...
9.6/10 Exceptional! (1,001 reviews)
"That the Langham is simply one of the finest hotel in Chicago. The rooms are outstanding with the decor and amenities. Definite 5 star hotel"

Reviewed on 12 Mar. 2024

The Langham, Chicago
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
108 East Superior Street, Chicago, IL
The price is CA $609 per night from Mar. 24 to Mar. 25
CA $609
per night
Mar. 24 - Mar. 25
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and a full-service spa. Our guests praise the helpful staff and the property condition ...
9.6/10 Exceptional! (1,003 reviews)
Amazing Hotel!
"Amazing! Friendly staff, beautiful room, and a spa on site!"

Reviewed on 17 Mar. 2024

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 CA $283 per night from Mar. 22 to Mar. 23
CA $283
per night
Mar. 22 - Mar. 23
Stay at this 4.5-star luxury hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,001 reviews)
"very nice"

Reviewed on 8 Mar. 2024

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 by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
511 North Columbus Drive, Chicago, IL
The price is CA $188 per night from Mar. 31 to Apr. 1
CA $188
per night
Mar. 31 - Apr. 1
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 ...
8.2/10 Very Good! (2,354 reviews)
"The breakfast is amazing!!!"

Reviewed on 16 Mar. 2024

Embassy Suites by Hilton 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 CA $189 per night from Mar. 31 to Apr. 1
CA $189
per night
Mar. 31 - Apr. 1
Stay at this 4-star spa hotel in Chicago. Enjoy a full-service spa, breakfast, and a 24-hour health club. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (1,126 reviews)
"Very busy in Chicago, St Patrick’s day!"

Reviewed on 17 Mar. 2024

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
The price is CA $168 per night from Mar. 31 to Apr. 1
CA $168
per night
Mar. 31 - Apr. 1
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, WiFi, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
7.8/10 Good! (2,119 reviews)
"There were some parts of the room near door handles that weren't clean."

Reviewed on 16 Mar. 2024

Embassy Suites by Hilton Chicago Downtown River North
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Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
The price is CA $236 per night from Mar. 31 to Apr. 1
CA $236
per night
Mar. 31 - Apr. 1
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the breakfast and the restaurant ...
8.8/10 Excellent! (3,481 reviews)
"Great place. Local to food and shopping"

Reviewed on 17 Mar. 2024

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

LondonHouse Chicago, Curio Collection by Hilton
JW Marriott Chicago
Fairmont Chicago at Millennium Park Gold Experience
Don't see what you're looking for?
See all available trips from WAS-All Airports to Chicago
View all trips
Prices and availability subject to change. Additional terms may apply.

Need a car after flight to Chicago?

Frequently asked questions

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 service this major city. Choose your favorite seat on one of these top carriers:

  • United Airlines
  • American Airlines
  • Southwest Airlines

What airport is best to fly into Chicago?
There are two airports servicing Chicago. If you fly into O’Hare Intl. Airport (ORD), you’ll be 26 kilometers from the city center. The second option is Chicago Airport, roughly 14 kilometers from all the action of the downtown area.
Where to stay in Chicago
Researched Chicago, planned your vacation outfits but haven’t yet locked in a place to stay? Travelocity can help. Select from 5,030 centrally located properties and start packing your bags!It’s time for your vacation! Why not treat yourself to luxury? If you’ve been dreaming of first-class service and soft, silky sheets, book the Palmer House a Hilton Hotel or the Silversmith Hotel Chicago Downtown. That being said, you wouldn’t go on vacation to stay in your room all week. If you’ve been looking for a more wallet-friendly option, consider the Hi Chicago or the Travelodge by Wyndham Downtown Chicago.Traveling is about absorbing those extraordinary sights. If McCormick Place is number one on your itinerary, you may want to stay a stone’s throw away. The Hyatt Regency McCormick Place is 0.16 kilometers away, while the Marriott Marquis Chicago is 0.32 kilometers away.
Places to visit in Chicago
With several famous sights in Chicago, you’re going to need to pack a pair of walking shoes. First and foremost on your travel schedule should be a journey to Art Institute of Chicago, and Millennium Park. After that, you might want to crank up the pace a bit as you shouldn’t take off without swinging by Skydeck Ledge, and Willis Tower.Avid sightseers should visit Chicago Cultural Center, and Buckingham Fountain. Would you like more things to do in this action-packed city? Merchandise Mart, and Wrigley Building will keep you occupied.0 Like some more ideas? 0 But that’s not all. 0
How to get through airport security fast when traveling to Chicago
Make your trip to Chicago a little easier by following these helpful tips and pointers:

  • Make sure you know the location of your travel ID and boarding pass. You don’t want to hold up the line when you’re asked to present them.
  • It’s helpful to know that belts with metal buckles can set off the body scanner’s alarms. If you have one on, you may be told to remove it before moving on.
  • Digital cameras, laptops and other electronic devices must be placed in separate tubs to be X-rayed.
  • When it comes to flying with liquids or gels, every passenger is allowed a quart-sized clear resealable bag to transport containers no bigger than 3.4 ounces (100 milliliters).
  • Undo your shoelaces as you approach the body scanner. Depending on the style of shoes you’ve got on, security may tell you to remove them.
  • Pack any multi-tools or other pointy metal items inside your checked luggage. Security personnel don’t permit these on the plane.

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.