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Chicago

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Chicago Flights as Low as $56

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, Apr 28 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$56 Roundtrip, found 11 hours ago
$56
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Tue, Apr 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, May 12, priced at $56 found 11 hours ago
Frontier Airlines
Tue, Apr 14 - Tue, Apr 21
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$56 Roundtrip, found 2 hours ago
$56
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Apr 14 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Apr 21, priced at $56 found 2 hours ago
Frontier Airlines
Sat, May 2 - Tue, May 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 5, priced at $56 just found
Spirit Airlines
Tue, May 12 - Sat, May 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$70 Roundtrip, found 3 hours ago
$70
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Tue, May 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, May 16, priced at $70 found 3 hours ago
Frontier Airlines
Mon, Mar 23 - Mon, Apr 13
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$80 Roundtrip, found 7 hours ago
$80
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Mon, Mar 23 from Dallas-Fort Worth Intl. to Midway Intl., returning Mon, Apr 13, priced at $80 found 7 hours ago
United
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 4 hours ago
$132
Roundtrip
found 4 hours ago
Select United flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $132 found 4 hours ago
Delta
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 4 hours ago
$132
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $132 found 4 hours ago
American Airlines
Sat, May 2 - Tue, May 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, just found
$137
Roundtrip
just found
Select American Airlines flight, departing Sat, May 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 5, priced at $137 just found
American Airlines
Mon, Apr 27 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$176 Roundtrip, found 2 hours ago
$176
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Mon, Apr 27 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, May 1, priced at $176 found 2 hours ago
Delta
Tue, May 12 - Wed, May 13
DAL
Love Field
MDW
Midway Intl.
$177 Roundtrip, found 7 hours ago
$177
Roundtrip
found 7 hours ago
Select Delta flight, departing Tue, May 12 from Love Field to Midway Intl., returning Wed, May 13, priced at $177 found 7 hours ago
Delta
Tue, May 12 - Sat, May 16
DAL
Love Field
ORD
O'Hare Intl.
$177 Roundtrip, found 1 hour ago
$177
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, May 12 from Love Field to O'Hare Intl., returning Sat, May 16, priced at $177 found 1 hour ago
United
Sat, Apr 11 - Sat, Apr 25
MCI
Kansas City Intl.
ORD
O'Hare Intl.
$177 Roundtrip, found 4 days ago
$177
Roundtrip
found 4 days ago
Select United flight, departing Sat, Apr 11 from Kansas City Intl. to O'Hare Intl., returning Sat, Apr 25, priced at $177 found 4 days ago
American Airlines
Fri, Apr 3 - Tue, Apr 7
MCI
Kansas City Intl.
RFD
Greater Rockford
$196 Roundtrip, found 4 days ago
$196
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Apr 3 from Kansas City Intl. to Greater Rockford, returning Tue, Apr 7, priced at $196 found 4 days ago
American Airlines
Fri, Apr 10 - Tue, Apr 14
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$197 Roundtrip, found 7 hours ago
$197
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Apr 10 from Dallas-Fort Worth Intl. to Greater Rockford, returning Tue, Apr 14, priced at $197 found 7 hours ago
Delta
Tue, May 5 - Wed, May 20
MCI
Kansas City Intl.
MDW
Midway Intl.
$237 Roundtrip, found 4 days ago
$237
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, May 5 from Kansas City Intl. to Midway Intl., returning Wed, May 20, priced at $237 found 4 days ago
Contour Airlines
Fri, May 22 - Mon, May 25
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$268 Roundtrip, found 16 hours ago
$268
Roundtrip
found 16 hours ago
Select Contour Airlines flight, departing Fri, May 22 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, May 25, priced at $268 found 16 hours ago

Cheap Flights to Chicago

Fall in love at first flight with your vacation to Chicago by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chicago on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chicago, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chicago

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chicago with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Chicago?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chicago are in April, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chicago?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Chicago.

What airport is best to fly into Chicago?

When you’re planning your trip to Chicago, convenience is the name of the game. Luckily, Chicago Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Chicago must-do list.

How much are flights to Chicago?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chicago on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $56, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chicago?

The trick to saving a stack of cash on your flight to Chicago? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $56 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$56

Last Minute Hotel Deals in Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (9,894 reviews)
We mainly go to Chicago for medical appointments and it is *so awesome* that you can actually open the windows here.That is the main reason we chose it. Because Dad has cancer we aired it out and then ran our own air purifier. No bad smells or anything, we're just being cautious because of his health. ...

Reviewed on Feb 27, 2026

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Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (3,422 reviews)
This is our new go-to in the city. Great location, very comfortable beds. Pillows are unusually small, but they brought more quickly. Large bathroom with double sinks. Breakfast buffet was excellent and plentiful. Shout out to Frank during our very late check-in. Very friendly, funny and was quick ...

Reviewed on Feb 27, 2026

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Hotel Riu Plaza Chicago
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
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,692 reviews)
Hotel is beautiful and located in the heart of everything. Starbucks outside is a plus. Breakfast is excellent and rooms are spacious. Wish they have a whirlpool

Reviewed on Feb 27, 2026

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Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (3,843 reviews)
The staff and space in the room was great! Location is outstanding!

Reviewed on Feb 27, 2026

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Hilton Chicago/Magnificent Mile Suites
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (3,271 reviews)
Not clean and the service bad

Reviewed on Feb 27, 2026

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Eurostars Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,655 reviews)
Very good!

Reviewed on Feb 27, 2026

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Hilton Chicago
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (3,102 reviews)
The room was amazing! I loved the view from it the Chicago city . The Hotel was presented beautifully and the pool was great too! I will definitely be coming back!

Reviewed on Feb 27, 2026

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Aloft Chicago Mag Mile
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (3,464 reviews)
The room was spotless. The front desk helped make sure my reservation was taken care of despite travel delays outside of my control. Highly recommended this property and their staff

Reviewed on Feb 24, 2026

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Hyatt Regency Chicago
See all 5,650 properties in 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.

Top Hotels With Free Airport Shuttle

Super 8 by Wyndham Chicago O'Hare Airport

Super 8 by Wyndham Chicago O'Hare Airport

3.5 out of 5
2951 Touhy Ave Elk Grove Village IL
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 ...
7.6/10 Good! (1,620 reviews)
Very nice ,,

Reviewed on Feb 27, 2026

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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
Book a stay at this golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.4/10 Good! (1,276 reviews)
Staff was rude experience was horrible.

Reviewed on Feb 27, 2026

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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
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 ...
9.2/10 Wonderful! (2,230 reviews)
Hotel and staff were great. Would highly recommend and will stay there again.

Reviewed on Feb 28, 2026

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Hampton Inn Chicago-O'Hare International Airport
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
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
8/10 Very Good! (1,003 reviews)
Checkin was painless as was catching the shuttle to ORD. The location is great as it’s about a five minute walk to the El stop for getting into the city easily.

Reviewed on Feb 25, 2026

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Holiday Inn Chicago O'Hare Area by IHG
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

4.5 out of 5
5300 N River Rd Rosemont IL
Book a stay at this luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful ...
9.4/10 Exceptional! (1,962 reviews)
The gym.

Reviewed on Feb 27, 2026

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Loews Chicago O'Hare Hotel
Carlton Inn Midway

Carlton Inn Midway

2 out of 5
4944 S Archer Ave Chicago IL
Book a stay at this business-friendly motel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.4/10 (1,001 reviews)
Sink was broke.

Reviewed on Feb 17, 2026

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Carlton Inn Midway
See all 5,650 properties in 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.