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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 - Wed, Apr 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$56 Roundtrip, found 5 hours ago
$56
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Apr 28 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Apr 29, priced at $56 found 5 hours ago
Spirit Airlines
Tue, Apr 28 - Wed, Apr 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$62 Roundtrip, found 5 hours ago
$62
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Tue, Apr 28 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Apr 29, priced at $62 found 5 hours ago
Frontier Airlines
Mon, Mar 23 - Mon, Apr 13
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$62 Roundtrip, found 10 hours ago
$62
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Mon, Mar 23 from Dallas-Fort Worth Intl. to Midway Intl., returning Mon, Apr 13, priced at $62 found 10 hours ago
Frontier Airlines
Tue, May 12 - Sat, May 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$64 Roundtrip, found 13 hours ago
$64
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, May 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, May 16, priced at $64 found 13 hours ago
Spirit Airlines
Tue, Apr 28 - Wed, Apr 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$67 Roundtrip, found 5 hours ago
$67
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Tue, Apr 28 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Apr 29, priced at $67 found 5 hours ago
Frontier Airlines
Fri, Apr 17 - Mon, Apr 27
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$67 Roundtrip, found 4 days ago
$67
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Apr 17 from Raleigh - Durham Intl. to O'Hare Intl., returning Mon, Apr 27, priced at $67 found 4 days ago
American Airlines
Tue, May 12 - Sat, May 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 13 hours ago
$157
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Tue, May 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, May 16, priced at $157 found 13 hours ago
United
Tue, May 12 - Sat, May 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 13 hours ago
$157
Roundtrip
found 13 hours ago
Select United flight, departing Tue, May 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, May 16, priced at $157 found 13 hours ago
Frontier Airlines
Wed, Apr 29 - Tue, May 12
RDU
Raleigh - Durham Intl.
MDW
Midway Intl.
$160 Roundtrip, found 5 days ago
$160
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Apr 29 from Raleigh - Durham Intl. to Midway Intl., returning Tue, May 12, priced at $160 found 5 days ago
Delta
Wed, Apr 29 - Wed, Apr 29
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$171 Roundtrip, found 3 days ago
$171
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Apr 29 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Apr 29, priced at $171 found 3 days ago
Delta
Sat, May 9 - Tue, May 12
DAL
Love Field
MDW
Midway Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 9 from Love Field to Midway Intl., returning Tue, May 12, priced at $177 found 1 day ago
Delta
Tue, May 12 - Sat, May 16
DAL
Love Field
ORD
O'Hare Intl.
$177 Roundtrip, found 13 hours ago
$177
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, May 12 from Love Field to O'Hare Intl., returning Sat, May 16, priced at $177 found 13 hours ago
American Airlines
Fri, Apr 10 - Tue, Apr 14
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days 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 3 days ago
JetBlue Airways
Tue, Mar 10 - Wed, Mar 25
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$241 Roundtrip, found 4 days ago
$241
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Mar 10 from Raleigh - Durham Intl. to O'Hare Intl., returning Wed, Mar 25, priced at $241 found 4 days ago
Contour Airlines
Fri, May 22 - Mon, May 25
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$268 Roundtrip, found 2 days ago
$268
Roundtrip
found 2 days 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 2 days ago
Alaska Airlines
Tue, Apr 28 - Wed, Apr 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$378 Roundtrip, found 5 hours ago
$378
Roundtrip
found 5 hours ago
Select Alaska Airlines flight, departing Tue, Apr 28 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Apr 29, priced at $378 found 5 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! (9,905 reviews)
Good

Reviewed on Mar 2, 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! (3,443 reviews)
The property was amazing the location was very convenient. I will recommend this hotel to anyone and everyone. I enjoy my day. Staff was amazing from check in to the bar. Thanks for a wonderful stay.

Reviewed on Mar 3, 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! (5,711 reviews)
Love the hotel just wish the pool water was warmer

Reviewed on Mar 2, 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! (3,863 reviews)
Close proximity to everything , only downside I would say is that they don’t tell you about the $100 deposit per day until after you book

Reviewed on Mar 3, 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! (3,287 reviews)
We had a great experience during our stay! The hotel was beautiful, clean, and very welcoming. Everything exceeded our expectations. We would definitely stay again!

Reviewed on Mar 3, 2026

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Eurostars Magnificent Mile
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! (3,121 reviews)
I loved the design of the hotel. Everybody was so helpful and friendly. I’ll definitely be back

Reviewed on Mar 3, 2026

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Aloft Chicago Mag 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! (2,659 reviews)
Not much food options and the Starbucks was extremely over priced .

Reviewed on Mar 2, 2026

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Hilton Chicago
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! (3,468 reviews)
I was there for a conference. I booked the deluxe king room in a high floor, at check in I was assured it was the room I b

Reviewed on Mar 1, 2026

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Hyatt Regency Chicago
See all 5,616 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! (1,623 reviews)
Breakfast is awful.

Reviewed on Mar 3, 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! (1,281 reviews)
Shuttles were great. Staff great. Hotel, dated but clean Pool nice. Breakfast available, cereal, bagels , ect. No hot food

Reviewed on Mar 2, 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! (2,235 reviews)
Clean and quiet. Front desk staff was cheerful, efficient and welcoming!

Reviewed on Mar 2, 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! (1,966 reviews)
Always.

Reviewed on Mar 1, 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 (1,003 reviews)
Room wasn’t properly cleaned and they ran out of towels had to go buy my own towels Lady at the front at check in had a nasty attitude

Reviewed on Feb 28, 2026

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Carlton Inn Midway
See all 5,616 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.