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Chicago

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Chicago Flights as Low as $78

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

Frontier Airlines
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, May 13, priced at $78 found 1 day ago
Spirit Airlines
Sat, May 2 - Mon, May 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$85 Roundtrip, found 5 days ago
$85
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, May 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, May 4, priced at $85 found 5 days ago
Spirit Airlines
Sat, Apr 25 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 22 hours ago
$108
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Sat, Apr 25 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, May 2, priced at $108 found 22 hours ago
Frontier Airlines
Fri, May 29 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, May 29 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 3, priced at $108 found 1 day ago
Frontier Airlines
Thu, May 28 - Sat, May 30
MCO
Orlando Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 22 hours ago
$117
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Thu, May 28 from Orlando Intl. to O'Hare Intl., returning Sat, May 30, priced at $117 found 22 hours ago
Frontier Airlines
Sat, May 2 - Fri, May 15
MCO
Orlando Intl.
MDW
Midway Intl.
$122 Roundtrip, found 4 days ago
$122
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, May 2 from Orlando Intl. to Midway Intl., returning Fri, May 15, priced at $122 found 4 days ago
Delta
Sat, May 9 - Tue, May 12
MCO
Orlando Intl.
MDW
Midway Intl.
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, May 9 from Orlando Intl. to Midway Intl., returning Tue, May 12, priced at $167 found 3 days ago
United
Sat, May 23 - Wed, Jun 10
MCO
Orlando Intl.
ORD
O'Hare Intl.
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select United flight, departing Sat, May 23 from Orlando Intl. to O'Hare Intl., returning Wed, Jun 10, priced at $190 found 1 day ago
American Airlines
Tue, May 19 - Tue, May 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$196 Roundtrip, found 2 days ago
$196
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, May 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 19, priced at $196 found 2 days ago
American Airlines
Wed, May 27 - Thu, May 28
MCO
Orlando Intl.
RFD
Greater Rockford
$221 Roundtrip, found 6 hours ago
$221
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to Greater Rockford, returning Thu, May 28, priced at $221 found 6 hours ago
Delta
Wed, May 20 - Wed, May 27
LAX
Los Angeles Intl.
MDW
Midway Intl.
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 20 from Los Angeles Intl. to Midway Intl., returning Wed, May 27, priced at $242 found 1 day ago
American Airlines
Thu, May 14 - Mon, May 18
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$282 Roundtrip, found 15 hours ago
$282
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Thu, May 14 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Mon, May 18, priced at $282 found 15 hours ago
American Airlines
Mon, May 25 - Tue, May 26
LAX
Los Angeles Intl.
RFD
Greater Rockford
$315 Roundtrip, found 3 days ago
$315
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, May 25 from Los Angeles Intl. to Greater Rockford, returning Tue, May 26, priced at $315 found 3 days ago
JetBlue Airways
Tue, May 26 - Wed, May 27
MCO
Orlando Intl.
ORD
O'Hare Intl.
$361 Roundtrip, found 22 hours ago
$361
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Tue, May 26 from Orlando Intl. to O'Hare Intl., returning Wed, May 27, priced at $361 found 22 hours ago
Alaska Airlines
Fri, May 29 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$364 Roundtrip, found 1 day ago
$364
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Fri, May 29 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 3, priced at $364 found 1 day ago
Sun Country Airlines
Sun, May 17 - Thu, May 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$491 Roundtrip, found 3 days ago
$491
Roundtrip
found 3 days ago
Select Sun Country Airlines flight, departing Sun, May 17 from Los Angeles Intl. to O'Hare Intl., returning Thu, May 21, priced at $491 found 3 days 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 $78, 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 $78 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$78

Last Minute Hotel Deals in 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! (4,155 reviews)
N/A

Reviewed on Apr 18, 2026

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Hilton Chicago/Magnificent Mile Suites
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! (5,859 reviews)
Clean and easy check in.

Reviewed on Apr 17, 2026

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Embassy Suites by Hilton Chicago Downtown River North
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! (10,142 reviews)
Our room was uncomfortably warm. They explained that the hotel is old and they put either the air conditioner on or the heat on in the hotel and since it was going to be cool the next day they had turned the heat on to begin heating the hotel for the next day. They did give us a fan and opened the ...

Reviewed on Apr 18, 2026

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Congress Plaza Hotel
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (2,626 reviews)
Stayed at this location for 3 days and had a great time. I saw where some people complained about the size of the room but it was spacious to me ( 1 king size bed). The hotel was in walking distance from a lot of the places we wanted to go to. Only down side was that the room did not have a closet ...

Reviewed on Apr 19, 2026

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Hotel Felix River North/Magnificent Mile
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! (3,885 reviews)
Room is super clean. Many options for breakfast.

Reviewed on Apr 19, 2026

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Hotel Riu Plaza Chicago
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! (2,266 reviews)
The room was spotless and the concierge service was excellent.

Reviewed on Apr 17, 2026

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Hilton Chicago O'Hare Airport
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (2,267 reviews)
Desayuno 👍 Staff 👍 Clean room 👍 Air conditioning 👍

Reviewed on Apr 18, 2026

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Holiday Inn Chicago Dwtn - The Mart by IHG
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,095 reviews)
Nice

Reviewed on Apr 19, 2026

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River Hotel
See all 5,600 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! (1,643 reviews)
Clean room and very kind staff.

Reviewed on Apr 18, 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! (1,368 reviews)
I dont know whos rating these places because this is a dump; tvs didnt work, pool and spa needs renovation, staff spreaded thin at night receptionist and van driver same person leaves guest waiting and calling with no response! Would not recommend

Reviewed on Apr 18, 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! (2,259 reviews)
Great staff !

Reviewed on Apr 18, 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! (1,005 reviews)
Room was clean, bed was comfortable, Check in/out was easy and having Bar Louie on property made food and entertainment easy. Will definitely stay here again.

Reviewed on Apr 16, 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! (2,028 reviews)
Nice hotel

Reviewed on Apr 18, 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 (1,001 reviews)
I didn't like that I rented rooms more than 3 times in a week and the tv was not working, the microwave did not work as well and the telephone in the room did not work also to call the front desk.

Reviewed on Apr 17, 2026

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Carlton Inn Midway
See all 5,600 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.