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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, May 5 - Tue, May 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$56 Roundtrip, found 8 hours ago
$56
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, May 5 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, May 19, priced at $56 found 8 hours ago
Frontier Airlines
Sat, May 16 - Tue, May 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$56 Roundtrip, found 3 hours ago
$56
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, May 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 19, priced at $56 found 3 hours ago
Frontier Airlines
Wed, Apr 8 - Tue, Apr 21
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$74 Roundtrip, found 6 days ago
$74
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Apr 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Apr 21, priced at $74 found 6 days ago
Spirit Airlines
Tue, May 5 - Wed, May 6
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$92 Roundtrip, found 1 day ago
$92
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, May 5 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, May 6, priced at $92 found 1 day ago
Frontier Airlines
Thu, Apr 16 - Mon, Apr 20
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$104 Roundtrip, found 1 day ago
$104
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Dallas-Fort Worth Intl. to Midway Intl., returning Mon, Apr 20, priced at $104 found 1 day ago
Delta
Sat, May 9 - Wed, Aug 26
BOS
Logan Intl.
ORD
O'Hare Intl.
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, May 9 from Logan Intl. to O'Hare Intl., returning Wed, Aug 26, priced at $127 found 2 days ago
United
Tue, Jun 30 - Tue, Aug 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jun 30 from Logan Intl. to O'Hare Intl., returning Tue, Aug 4, priced at $137 found 1 day ago
American Airlines
Wed, Jul 1 - Tue, Aug 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 2 hours ago
$137
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Jul 1 from Logan Intl. to O'Hare Intl., returning Tue, Aug 4, priced at $137 found 2 hours ago
JetBlue Airways
Wed, May 27 - Thu, May 28
BOS
Logan Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 13 hours ago
$138
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Wed, May 27 from Logan Intl. to O'Hare Intl., returning Thu, May 28, priced at $138 found 13 hours ago
Delta
Sat, May 2 - Sat, May 9
DAL
Love Field
MDW
Midway Intl.
$180 Roundtrip, found 2 days ago
$180
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, May 2 from Love Field to Midway Intl., returning Sat, May 9, priced at $180 found 2 days ago
Delta
Tue, May 12 - Sat, May 16
DAL
Love Field
ORD
O'Hare Intl.
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, May 12 from Love Field to O'Hare Intl., returning Sat, May 16, priced at $187 found 1 day ago
American Airlines
Fri, Apr 10 - Tue, Apr 14
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$230 Roundtrip, found 5 hours ago
$230
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Fri, Apr 10 from Dallas-Fort Worth Intl. to Greater Rockford, returning Tue, Apr 14, priced at $230 found 5 hours ago
American Airlines
Mon, Apr 27 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$263 Roundtrip, found 5 hours ago
$263
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Mon, Apr 27 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, May 1, priced at $263 found 5 hours ago
Contour Airlines
Wed, Apr 29 - Mon, May 18
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$272 Roundtrip, found 21 hours ago
$272
Roundtrip
found 21 hours ago
Select Contour Airlines flight, departing Wed, Apr 29 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, May 18, priced at $272 found 21 hours ago
Delta
Tue, Jun 30 - Tue, Aug 4
BOS
Logan Intl.
MDW
Midway Intl.
$289 Roundtrip, found 19 hours ago
$289
Roundtrip
found 19 hours ago
Select Delta flight, departing Tue, Jun 30 from Logan Intl. to Midway Intl., returning Tue, Aug 4, priced at $289 found 19 hours ago
American Airlines
Tue, Jun 30 - Tue, Aug 4
BOS
Logan Intl.
RFD
Greater Rockford
$437 Roundtrip, found 21 hours ago
$437
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Tue, Jun 30 from Logan Intl. to Greater Rockford, returning Tue, Aug 4, priced at $437 found 21 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 May, 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! (9,938 reviews)
Good: Clean; friendly staff. Bad: hot water stopped working at some point; safe was not working; lightbulb kept flickering; ice machine was broken on the 10th floor

Reviewed on Mar 9, 2026

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Congress Plaza 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
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! (5,745 reviews)
Love the complimentary drinks !

Reviewed on Mar 10, 2026

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Embassy Suites by Hilton Chicago Downtown River North
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! (3,499 reviews)
It was great and hotels.com is just as great

Reviewed on Mar 10, 2026

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Hotel Riu Plaza Chicago
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! (3,902 reviews)
Yes everything was magnificent

Reviewed on Mar 10, 2026

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Hilton Chicago/Magnificent Mile Suites
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,232 reviews)
Great!!!

Reviewed on Mar 8, 2026

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Hilton Chicago O'Hare Airport
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! (3,314 reviews)
Great stay. Staff was slightly inattentive at times with requests for things to room.

Reviewed on Mar 9, 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! (2,675 reviews)
my stay was excellent, the staff and our room where fantastic.

Reviewed on Mar 9, 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! (3,147 reviews)
Great location, nice place!

Reviewed on Mar 10, 2026

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Aloft Chicago Mag Mile
See all 5,572 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! (1,633 reviews)
Place was terrible

Reviewed on Mar 9, 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! (1,288 reviews)
I stayed there for 1 night. Friday night to Saturday morning. Staff was nice, informative, and polite. The pool it nice but not heated. It wasn't swimming vibe. The hot tub was nice and hot. The breakfast was good. Egg sausage waffles a nice warm cup of coffee. Great selection on coffees, juice, ...

Reviewed on Mar 8, 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! (2,248 reviews)
The hotel was adequate and comfortable for our stay. It doesn’t have many bells and whistles, but the rooms were clean, the beds were comfortable, and the soundproofing was good, which made for a restful night’s sleep. Breakfast was decent and provided enough variety to start the day. Overall, it’s ...

Reviewed on Mar 10, 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! (1,008 reviews)
Air worked ok

Reviewed on Mar 3, 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! (1,983 reviews)
Beautiful hotel, great staff, easy location for food and drinks

Reviewed on Mar 9, 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 (1,006 reviews)
Convenient location to train station and airport. Friendly and helpful staff. Room was good sized with dining area and equipped with all the conviences. Unfortunately the hot water was not working the night we stayed and the tub was a little cringy (not sure if I would have wanted to use it even ...

Reviewed on Mar 9, 2026

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Carlton Inn Midway
See all 5,572 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.