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Chicago

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Chicago Flights as Low as $88

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

Frontier Airlines
Mon, Aug 25 - Thu, Aug 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 3 hours ago
$88
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, Aug 25 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Aug 28, priced at $88 found 3 hours ago
Frontier Airlines
Mon, Aug 4 - Thu, Aug 7
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$90 Roundtrip, found 5 days ago
$90
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Aug 4 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Aug 7, priced at $90 found 5 days ago
Spirit Airlines
Wed, Jul 23 - Wed, Jul 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jul 23 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $100 found 2 days ago
Frontier Airlines
Tue, Aug 5 - Sat, Aug 9
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$101 Roundtrip, found 1 day ago
$101
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 5 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Aug 9, priced at $101 found 1 day ago
Frontier Airlines
Tue, Jul 29 - Thu, Aug 7
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 2 days ago
$112
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jul 29 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Aug 7, priced at $112 found 2 days ago
Frontier Airlines
Mon, Jul 21 - Sat, Jul 26
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$121 Roundtrip, found 6 days ago
$121
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Jul 21 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Jul 26, priced at $121 found 6 days ago
Spirit Airlines
Sat, Sep 27 - Tue, Sep 30
LGA
LaGuardia
ORD
O'Hare Intl.
$126 Roundtrip, found 13 hours ago
$126
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Sat, Sep 27 from LaGuardia to O'Hare Intl., returning Tue, Sep 30, priced at $126 found 13 hours ago
Spirit Airlines
Tue, Nov 4 - Tue, Nov 11
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Nov 4 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Nov 11, priced at $132 found 1 day ago
United
Sat, Sep 27 - Tue, Sep 30
LGA
LaGuardia
ORD
O'Hare Intl.
$147 Roundtrip, found 13 hours ago
$147
Roundtrip
found 13 hours ago
Select United flight, departing Sat, Sep 27 from LaGuardia to O'Hare Intl., returning Tue, Sep 30, priced at $147 found 13 hours ago
Delta
Sat, Sep 27 - Sat, Sep 27
LGA
LaGuardia
ORD
O'Hare Intl.
$152 Roundtrip, found 2 days ago
$152
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep 27 from LaGuardia to O'Hare Intl., returning Sat, Sep 27, priced at $152 found 2 days ago
American Airlines
Tue, Sep 9 - Tue, Sep 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 1 day ago
$152
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Sep 9, priced at $152 found 1 day ago
Contour Airlines
Mon, Sep 8 - Thu, Sep 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Mon, Sep 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $189 found 2 days ago
Delta
Tue, Sep 9 - Tue, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 9, priced at $191 found 1 day ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 found 1 day ago
Delta
Tue, Jul 29 - Tue, Aug 5
LGA
LaGuardia
MDW
Midway Intl.
$221 Roundtrip, found 22 hours ago
$221
Roundtrip
found 22 hours ago
Select Delta flight, departing Tue, Jul 29 from LaGuardia to Midway Intl., returning Tue, Aug 5, priced at $221 found 22 hours ago
Frontier Airlines
Tue, Jul 15 - Fri, Jul 18
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$237 Roundtrip, found 19 hours ago
$237
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Tue, Jul 15 from Newark Liberty Intl. Airport to Midway Intl., returning Fri, Jul 18, priced at $237 found 19 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 August, 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 $88, 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 $88 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$80

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 free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,937 reviews)
"We enjoyed the location."

Reviewed on Jul 1, 2025

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Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (1,956 reviews)
"Top tier hospitality!"

Reviewed on Jul 1, 2025

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InterContinental Chicago Magnificent Mile by IHG
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 ...
8.8/10 Excellent! (2,365 reviews)
"The customer service was impeccable! Steven and Rocky were both very helpful and friendly during our stay!"

Reviewed on Jul 1, 2025

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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 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,321 reviews)
Great Family Stay
"Great for a Family of 6"

Reviewed on Jul 2, 2025

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Embassy Suites by Hilton Chicago Downtown River North
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (3,269 reviews)
"Such a fun hotel! Loved the theme carrried through all aspects of the brand and design of the hotel. Super clean. Room might be a bit small for 2. I found for 1 person, it was perfect. Great location!"

Reviewed on Jul 2, 2025

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citizenM Chicago Downtown
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection
3.5 out of 5
105 E Delaware Pl, Chicago, IL
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
8.2/10 Very Good! (3,436 reviews)
"I really enjoyed the hotel! Staff were very attentive to my needs and friendly!"

Reviewed on Jul 1, 2025

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The Whitehall Hotel, BW Premier Collection
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and ...
8.8/10 Excellent! (2,327 reviews)
"Great location , amazing property"

Reviewed on Jul 3, 2025

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Swissotel - Chicago
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (1,823 reviews)
Loved this hotel!
"This hotel was just perfect! The staff were all very friendly, especially service desk. The rooms were well stocked. The room was a bit small, but it didn't bother us. Within walking distance to everything! Will definitely be staying here again. Thank you for a great experience ❤️"

Reviewed on Jul 2, 2025

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Hotel Felix River North/Magnificent Mile
See all 5,291 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
Stay at this 3.5-star business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
7.8/10 Good! (1,277 reviews)
"Quite"

Reviewed on Jun 30, 2025

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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
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
6.8/10 (1,028 reviews)
"I had a great stay"

Reviewed on Jul 1, 2025

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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 ...
9/10 Wonderful! (1,944 reviews)
"Great stay- close to airport."

Reviewed on Jul 1, 2025

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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
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
7.6/10 Good! (1,001 reviews)
"Good"

Reviewed on Jul 1, 2025

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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
Stay at this 4.5-star luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the ...
9.4/10 Exceptional! (1,867 reviews)
"Loved everything!"

Reviewed on Jun 30, 2025

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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)
"The stairs needed repair there were rotted parts in stairs"

Reviewed on Jun 11, 2025

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Carlton Inn Midway
See all 5,291 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.