Cheap Flight Deals to Chicago IL from CA $166

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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 $86 and CA $166 for one-way flights to Chicago for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
ATLChicagoMay 22 to May 25CA $86
EWRChicagoMay 29 to June 2CA $112
LAXChicagoJune 5 to June 25CA $154
DFWChicagoJune 14 to June 21CA $179
EWRChicagoMay 30 to June 2CA $306
ATLChicagoJune 27 to June 30CA $325
LAXChicagoJune 5 to June 25CA $361
DALChicagoJuly 25 to August 22CA $643
PVGChicagoJuly 21 to August 19CA $1,595
PEKChicagoJune 19 to July 4CA $1,630
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
EWRChicagoMay 18 to May 19CA $239
ATLChicagoMay 16 to May 18CA $480
LAXChicagoMay 17 to May 17CA $493
ATLChicagoMay 16 to May 18CA $796
PEKChicagoMay 17 to May 23CA $2,345
*Prices include taxes and fees

Your guide to flights to Chicago, IL

American Airlines, Air Canada 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 CA $86 and CA $2,345. Prices vary, but for the best fares, travel in September 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 $86. 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. 

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 $104 per night from May 26 to May 27
CA $104
CA $147 total
May 26 - May 27
includes taxes & fees
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. ...
7.8/10 Good! (1,796 reviews)
"Excellent place if just need a place to sleep in a clean , safe area . I would suggest to bring ear plugs if you have to share a room in dorm ."

Reviewed on May 12, 2025

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 $116 per night from May 27 to May 28
CA $116
CA $136 total
May 27 - May 28
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7/10 Good! (2,145 reviews)
"The staff was great. They help me with everything from events and how to get around in town. I will stay again"

Reviewed on May 11, 2025

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 $65 per night from May 21 to May 22
CA $65
CA $74 total
May 21 - May 22
includes taxes & fees
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 ...
7.8/10 Good! (1,445 reviews)
"No where to eat"

Reviewed on May 11, 2025

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 $154 per night from May 26 to May 27
CA $154
CA $181 total
May 26 - May 27
includes taxes & fees
Stay at this motel in Chicago. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the helpful staff and the convenient parking ...
8.8/10 Excellent! (1,005 reviews)
"It’s around everything and are able to take the cta bus and trains very convenient"

Reviewed on May 9, 2025

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 $101 per night from May 14 to May 15
CA $101
CA $114 total
May 14 - May 15
includes taxes & fees
Book a 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 ...
7.8/10 Good! (1,194 reviews)
Great Value
"Five stars for exceeding expectations for a low priced motel in industrial area. Great location to access Chicago and north and west suburbs. Comfortable, clean, and quiet. Efficient front desk. Older property that shows its age, but I saw some rooms getting remodeled. Highly recommended for low ..."

Reviewed on May 9, 2025

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 E Grand Avenue, Bensenville, IL
The price is CA $118 per night from Jun. 11 to Jun. 12
CA $118
CA $134 total
Jun 11 - Jun 12
includes taxes & fees
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
6.8/10 (1,008 reviews)
Weekend stay
"Elevator broke had to carry luggage up/down 3 flights, pool area had clumps of hair near some drains. And was fine until kids arrived, cut my pool time early. Room or suite was comfortable and nice. Staff was friendly and helpful"

Reviewed on May 11, 2025

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 $153 per night from May 22 to May 23
CA $153
CA $175 total
May 22 - May 23
includes taxes & fees
Book a 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 ...
9/10 Wonderful! (1,876 reviews)
"Breakfast food could use improvement. No meat choices."

Reviewed on May 11, 2025

Hampton Inn Chicago-O'Hare International Airport
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Holiday Inn Chicago O'Hare Area by IHG

Holiday Inn Chicago O'Hare Area by IHG

3 out of 5
5615 North Cumberland Avenue, Chicago, IL
The price is CA $130 per night from May 26 to May 27
CA $130
CA $153 total
May 26 - May 27
includes taxes & fees
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
7.6/10 Good! (1,008 reviews)
"Good job"

Reviewed on May 10, 2025

Holiday Inn Chicago O'Hare Area by IHG
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 $624 per night from May 26 to May 27
CA $624
CA $732 total
May 26 - May 27
includes taxes & fees
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,590 reviews)
"Great place to stay on Chicago!"

Reviewed on May 10, 2025

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 $723 per night from May 27 to May 28
CA $723
CA $849 total
May 27 - May 28
includes taxes & fees
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (1,001 reviews)
"Great!"

Reviewed on May 5, 2025

The Langham, Chicago
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
108 East Superior Street, Chicago, IL
The price is CA $804 per night from May 26 to May 27
CA $804
CA $943 total
May 26 - May 27
includes taxes & fees
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
9.8/10 Exceptional! (1,000 reviews)
"This is by far the nicest hotel in Chicago,"

Reviewed on May 2, 2025

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 $418 per night from May 25 to May 26
CA $418
CA $525 total
May 25 - May 26
includes taxes & fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our ...
9.4/10 Exceptional! (1,004 reviews)
"Favorite in Chicago!"

Reviewed on May 11, 2025

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 $263 per night from May 27 to May 28
CA $263
CA $309 total
May 27 - May 28
includes taxes & fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (2,665 reviews)
"Very comfortable stay. No issues at all"

Reviewed on May 11, 2025

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 $211 per night from May 26 to May 27
CA $211
CA $283 total
May 26 - May 27
includes taxes & fees
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,715 reviews)
"We had an exceptional stay! I planned this trip to celebrate my husband’s 40th birthday, and the staff went above and beyond to make it truly special. From the moment we arrived, everyone was incredibly attentive and welcoming. Jay and his assistant Luis really stood out—Jay even made sure we knew ..."

Reviewed on May 11, 2025

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 $225 per night from May 26 to May 27
CA $225
CA $264 total
May 26 - May 27
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (4,031 reviews)
"I would definitely stay here again. Everything is comfortable and clean. Wish I had more time to explore the area more."

Reviewed on May 10, 2025

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 $293 per night from May 26 to May 27
CA $293
CA $386 total
May 26 - May 27
includes taxes & fees
Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (3,226 reviews)
"Wonderful stay in a great location!"

Reviewed on May 12, 2025

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

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Trump International Hotel & Tower Chicago
The Peninsula Chicago
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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.

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 hotelOpens in a new window 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.