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Chicago

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Chicago Flights as Low as $72

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

Frontier Airlines
Tue, Apr 28 - Tue, May 5
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$72 Roundtrip, found 2 hours ago
$72
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Apr 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, May 5, priced at $72 found 2 hours ago
Frontier Airlines
Wed, May 6 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 8 hours ago
$72
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, May 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 12, priced at $72 found 8 hours ago
Spirit Airlines
Tue, Apr 28 - Wed, Apr 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$86 Roundtrip, found 2 days ago
$86
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Apr 28 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Apr 29, priced at $86 found 2 days ago
Frontier Airlines
Wed, May 6 - Tue, May 19
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$88 Roundtrip, found 13 hours ago
$88
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Wed, May 6 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, May 19, priced at $88 found 13 hours ago
Frontier Airlines
Tue, May 12 - Tue, May 19
DEN
Denver Intl.
ORD
O'Hare Intl.
$92 Roundtrip, found 2 hours ago
$92
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, May 12 from Denver Intl. to O'Hare Intl., returning Tue, May 19, priced at $92 found 2 hours ago
Bargain Flight
Sun, Jun 14 - Thu, Jun 18
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 17 hours ago
$167
Roundtrip
found 17 hours ago
Select Bargain Flight flight, departing Sun, Jun 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Jun 18, priced at $167 found 17 hours ago
Frontier Airlines
Tue, May 5 - Sat, May 9
DEN
Denver Intl.
MDW
Midway Intl.
$184 Roundtrip, found 4 days ago
$184
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, May 5 from Denver Intl. to Midway Intl., returning Sat, May 9, priced at $184 found 4 days ago
American Airlines
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $200 found 1 day ago
Delta
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $200 found 1 day ago
Delta
Tue, Apr 21 - Tue, Apr 28
DAL
Love Field
MDW
Midway Intl.
$225 Roundtrip, found 11 hours ago
$225
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Apr 21 from Love Field to Midway Intl., returning Tue, Apr 28, priced at $225 found 11 hours ago
Delta
Tue, Apr 28 - Wed, Apr 29
DAL
Love Field
ORD
O'Hare Intl.
$225 Roundtrip, found 10 hours ago
$225
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Apr 28 from Love Field to O'Hare Intl., returning Wed, Apr 29, priced at $225 found 10 hours ago
American Airlines
Mon, Apr 27 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$236 Roundtrip, found 1 day ago
$236
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Apr 27 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, May 1, priced at $236 found 1 day ago
American Airlines
Fri, Apr 10 - Tue, Apr 14
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$267 Roundtrip, just found
$267
Roundtrip
just found
Select American Airlines flight, departing Fri, Apr 10 from Dallas-Fort Worth Intl. to Greater Rockford, returning Tue, Apr 14, priced at $267 just found
American Airlines
Fri, Apr 10 - Sun, Apr 12
DEN
Denver Intl.
RFD
Greater Rockford
$295 Roundtrip, found 4 days ago
$295
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Apr 10 from Denver Intl. to Greater Rockford, returning Sun, Apr 12, priced at $295 found 4 days ago
Contour Airlines
Fri, Jun 19 - Mon, Jun 22
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$335 Roundtrip, found 6 days ago
$335
Roundtrip
found 6 days ago
Select Contour Airlines flight, departing Fri, Jun 19 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Jun 22, priced at $335 found 6 days ago
Alaska Airlines
Tue, May 12 - Tue, May 19
DEN
Denver Intl.
ORD
O'Hare Intl.
$411 Roundtrip, found 2 hours ago
$411
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Tue, May 12 from Denver Intl. to O'Hare Intl., returning Tue, May 19, priced at $411 found 2 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 15 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 $72, 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 $72 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$62

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! (9,969 reviews)
Room was clean and comfortable. The view was great from our room. The building itself (hallways, corridors) could use a lot of repairs and freshening up, but it’s a massive historic building, that’s to be expected.

Reviewed on Mar 20, 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! (3,570 reviews)
We had a very pleasant stay overall. Wonderful location, nice room, very clean. Staff were consistently warm, attentive, and eager to help with anything we needed. Breakfast was another highlight. There was a great variety of options, with something for everyone, and everything we tried was fresh ...

Reviewed on Mar 20, 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! (5,749 reviews)
The location was great, near plenty of restaurants and shopping. The room was a great layout plenty of space.

Reviewed on Mar 19, 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! (3,943 reviews)
The bathrooms need updating. The shower floor is chipping. There are cracks between the wall and floor of shower. There is water damage on the base of bathroom door. Which is "bubbling" up. One can see that instead of replacing door. It has been painted over repeatedly. The wall socket near the nightstand ...

Reviewed on Mar 20, 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! (2,228 reviews)
The hotel had no electricity upon arrival, inexplicably as there were no severe weather conditions. I was handed two glow sticks to be able to guide my way around the hotel and my room. You can’t make this stuff up. The fact that there was nothing provided to compensate for the matter (discount, ...

Reviewed on Mar 19, 2026

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Hilton Chicago O'Hare Airport
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,740 reviews)
The staff was super nice, hotel was quiet and room was comfy. Very close to navy pier, within walking distance. Would be a great hotel for the summertime.

Reviewed on Mar 20, 2026

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The Wade
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! (3,142 reviews)
Convenient location, good rooms, good wifi

Reviewed on Mar 19, 2026

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Aloft Chicago Mag Mile
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! (3,315 reviews)
It was ok

Reviewed on Mar 18, 2026

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Eurostars Magnificent Mile
See all 5,533 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! (1,625 reviews)
It's a decent place. Quite old. Good for a 1-2 day stay. For the price, it's good. It's not a Marriott or Hilton, so that standard is different. Breakfast was basically just some waffles and bread.

Reviewed on Mar 19, 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! (1,306 reviews)
Clean room, nice staff

Reviewed on Mar 19, 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! (2,243 reviews)
Great staff, airport shuttle,

Reviewed on Mar 20, 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 ...
8.2/10 Very Good! (1,003 reviews)
Good

Reviewed on Mar 20, 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! (1,989 reviews)
Everything was great

Reviewed on Mar 19, 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 ...
6.2/10 (1,002 reviews)
Room is dirty, bad cleaning. Gave us a single bedroom as we ordered double bedroom online, and they refused to give any refund. Suck motel overall.

Reviewed on Mar 18, 2026

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Carlton Inn Midway
See all 5,533 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.