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Chicago

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Chicago Flights as Low as $108

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

Frontier Airlines
Tue, Dec 15 - Tue, Jan 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 1 hour ago
$108
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Dec 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jan 5, priced at $108 found 1 hour ago
Frontier Airlines
Tue, Jan 19 - Wed, Feb 10
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$128 Roundtrip, just found
$128
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Jan 19 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Feb 10, priced at $128 just found
Bargain Flight
Wed, Dec 2 - Thu, Dec 3
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$187 Roundtrip, found 2 hours ago
$187
Roundtrip
found 2 hours ago
Select Bargain Flight flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Dec 3, priced at $187 found 2 hours ago
Southwest Airlines
Tue, Jan 19 - Wed, Feb 10
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Jan 19 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Feb 10, priced at $197 just found
Delta
Tue, Dec 15 - Tue, Jan 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Dec 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jan 5, priced at $197 found 1 hour ago
United
Tue, Dec 29 - Wed, Jan 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 16 hours ago
$257
Roundtrip
found 16 hours ago
Select United flight, departing Tue, Dec 29 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jan 6, priced at $257 found 16 hours ago
Delta
Tue, Jan 5 - Tue, Jan 19
LAX
Los Angeles Intl.
MDW
Midway Intl.
$274 Roundtrip, found 1 day ago
$274
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 5 from Los Angeles Intl. to Midway Intl., returning Tue, Jan 19, priced at $274 found 1 day ago
JetBlue Airways
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$280 Roundtrip, found 2 hours ago
$280
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $280 found 2 hours ago
American Airlines
Tue, Dec 15 - Tue, Jan 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$297 Roundtrip, found 1 hour ago
$297
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Dec 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jan 5, priced at $297 found 1 hour ago
Alaska Airlines
Thu, Dec 24 - Wed, Jan 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$328 Roundtrip, found 11 hours ago
$328
Roundtrip
found 11 hours ago
Select Alaska Airlines flight, departing Thu, Dec 24 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jan 6, priced at $328 found 11 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Dec 29 - Sat, Jan 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$448 Roundtrip, found 1 day ago
$448
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Dec 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Jan 2, priced at $448 found 1 day ago
Sun Country Airlines
Sun, Dec 20 - Fri, Dec 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$686 Roundtrip, found 1 hour ago
$686
Roundtrip
found 1 hour ago
Select Sun Country Airlines flight, departing Sun, Dec 20 from Los Angeles Intl. to O'Hare Intl., returning Fri, Dec 25, priced at $686 found 1 hour ago
United
Thu, Nov 19 - Mon, Nov 23
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,193 Roundtrip, found 4 hours ago
$1,193
Roundtrip
found 4 hours ago
Select United flight, departing Thu, Nov 19 from Pudong Intl. to O'Hare Intl., returning Mon, Nov 23, priced at $1,193 found 4 hours ago
Air Canada
Tue, Dec 15 - Fri, Jan 1
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,300 Roundtrip, just found
$1,300
Roundtrip
just found
Select Air Canada flight, departing Tue, Dec 15 from Pudong Intl. to O'Hare Intl., returning Fri, Jan 1, priced at $1,300 just found
Korean Air
Tue, Dec 15 - Fri, Jan 1
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,312 Roundtrip, just found
$1,312
Roundtrip
just found
Select Korean Air flight, departing Tue, Dec 15 from Pudong Intl. to O'Hare Intl., returning Fri, Jan 1, priced at $1,312 just found
EVA Airways
Thu, Nov 19 - Mon, Nov 23
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,500 Roundtrip, found 4 hours ago
$1,500
Roundtrip
found 4 hours ago
Select EVA Airways flight, departing Thu, Nov 19 from Pudong Intl. to O'Hare Intl., returning Mon, Nov 23, priced at $1,500 found 4 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 December, 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 $108, 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 $108 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$108

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! (10,091 reviews)
"Great overall hotel! Nice and cozy!"

Reviewed on Nov 15, 2026

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Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (2,713 reviews)
"Paper thin walls, super outdated everything, lumpy mattress, noisy AC, there was dirt or something in our bath tub when we arrived, and the lobby BLARED music all evening, even when we left for the airport at 4am"

Reviewed on Nov 15, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
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 ...
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River Hotel
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 free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
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The Wade
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (2,622 reviews)
"Thank you to Raymond and Ebony for their excellent customer service. There is nothing quite like being welcomed with a smile."

Reviewed on Nov 15, 2026

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The Chicago Hotel Collection - 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 ...
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Hilton Chicago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
172 W Adams St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the ...
8.6/10 Excellent! (1,002 reviews)
"A"

Reviewed on Nov 12, 2026

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THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
71 E Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
9.4/10 Exceptional! (3,699 reviews)
"Cleanliness"

Reviewed on Nov 15, 2026

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The Royal Sonesta Chicago Downtown
See all 5,371 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 ...
7.4/10 Good! (2,072 reviews)
"The indoor pool was drained. No prior notice of this was made in their advertisement of amenities. Additionally, their vending machines were poorly stocked and the cash input kept rejecting dollar bills. The hallway carpet and room carpet is heavily worn and stained. The bathroom door closes but ..."

Reviewed on Nov 15, 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 ...
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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 ...
9.4/10 Exceptional! (2,414 reviews)
"Very good"

Reviewed on Nov 15, 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 ...
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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! (2,300 reviews)
"Great hotel"

Reviewed on Nov 14, 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 ...
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Carlton Inn Midway
See all 5,371 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.