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Chicago

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Chicago Flights as Low as $80

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

Spirit Airlines
Fri, Jan 31 - Sun, Feb 2
MCO
Orlando Intl.
ORD
O'Hare Intl.
$80 Roundtrip, found 3 days ago
$80
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Fri, Jan 31 from Orlando Intl. to O'Hare Intl., returning Sun, Feb 2, priced at $80 found 3 days ago
Frontier Airlines
Fri, Jan 31 - Sun, Feb 2
MCO
Orlando Intl.
ORD
O'Hare Intl.
$94 Roundtrip, found 3 days ago
$94
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Jan 31 from Orlando Intl. to O'Hare Intl., returning Sun, Feb 2, priced at $94 found 3 days ago
Frontier Airlines
Fri, Jan 24 - Mon, Jan 27
MCO
Orlando Intl.
MDW
Midway Intl.
$103 Roundtrip, found 3 days ago
$103
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Jan 24 from Orlando Intl. to Midway Intl., returning Mon, Jan 27, priced at $103 found 3 days ago
Spirit Airlines
Wed, Feb 12 - Wed, Feb 19
DTW
Detroit Metropolitan Wayne County
ORD
O'Hare Intl.
$116 Roundtrip, found 3 days ago
$116
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Feb 12 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Wed, Feb 19, priced at $116 found 3 days ago
United
Wed, Mar 5 - Wed, Mar 12
MCO
Orlando Intl.
ORD
O'Hare Intl.
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago
Select United flight, departing Wed, Mar 5 from Orlando Intl. to O'Hare Intl., returning Wed, Mar 12, priced at $177 found 6 days ago
American Airlines
Wed, Mar 5 - Wed, Mar 12
MCO
Orlando Intl.
ORD
O'Hare Intl.
$194 Roundtrip, found 6 days ago
$194
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Mar 5 from Orlando Intl. to O'Hare Intl., returning Wed, Mar 12, priced at $194 found 6 days ago
JetBlue Airways
Mon, Mar 24 - Sat, Mar 29
MCO
Orlando Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Mon, Mar 24 from Orlando Intl. to O'Hare Intl., returning Sat, Mar 29, priced at $197 found 2 days ago
Delta
Sat, Feb 15 - Sat, Feb 15
DTW
Detroit Metropolitan Wayne County
ORD
O'Hare Intl.
$213 Roundtrip, found 3 days ago
$213
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Feb 15 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Sat, Feb 15, priced at $213 found 3 days ago
Frontier Airlines
Thu, Jan 23 - Fri, Jan 24
DTW
Detroit Metropolitan Wayne County
MDW
Midway Intl.
$330 Roundtrip, found 3 days ago
$330
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Jan 23 from Detroit Metropolitan Wayne County to Midway Intl., returning Fri, Jan 24, priced at $330 found 3 days ago
American Airlines
Tue, Feb 25 - Sun, Mar 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$933 Roundtrip, found 3 days ago
$933
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Feb 25 from Pudong Intl. to O'Hare Intl., returning Sun, Mar 2, priced at $933 found 3 days ago
Cathay Pacific
Tue, Feb 25 - Sun, Mar 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,191 Roundtrip, found 3 days ago
$1,191
Roundtrip
found 3 days ago
Select Cathay Pacific flight, departing Tue, Feb 25 from Pudong Intl. to O'Hare Intl., returning Sun, Mar 2, priced at $1,191 found 3 days ago
Etihad Airways
Wed, May 7 - Tue, Jun 3
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,245 Roundtrip, found 1 day ago
$1,245
Roundtrip
found 1 day ago
Select Etihad Airways flight, departing Wed, May 7 from Pudong Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $1,245 found 1 day ago
Lufthansa
Tue, May 6 - Tue, May 27
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,258 Roundtrip, found 1 day ago
$1,258
Roundtrip
found 1 day ago
Select Lufthansa flight, departing Tue, May 6 from Pudong Intl. to O'Hare Intl., returning Tue, May 27, priced at $1,258 found 1 day ago
All Nippon Airways
Tue, May 6 - Tue, May 27
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,259 Roundtrip, found 1 day ago
$1,259
Roundtrip
found 1 day ago
Select All Nippon Airways flight, departing Tue, May 6 from Pudong Intl. to O'Hare Intl., returning Tue, May 27, priced at $1,259 found 1 day ago
Swiss International Air Lines
Thu, May 1 - Sun, May 18
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,265 Roundtrip, found 1 day ago
$1,265
Roundtrip
found 1 day ago
Select Swiss International Air Lines flight, departing Thu, May 1 from Pudong Intl. to O'Hare Intl., returning Sun, May 18, priced at $1,265 found 1 day ago
Korean Air
Tue, Feb 25 - Sun, Mar 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,305 Roundtrip, found 3 days ago
$1,305
Roundtrip
found 3 days ago
Select Korean Air flight, departing Tue, Feb 25 from Pudong Intl. to O'Hare Intl., returning Sun, Mar 2, priced at $1,305 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 January, 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 $80, 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 $80 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$58

Last Minute Hotel Deals in Chicago

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $126 per night from Jan 22 to Jan 23
$126
includes taxes & fees
Jan 22 - Jan 23
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! (8,400 reviews)
"Very clean. Friendly staff. Security was always alert. Decent gym for a hotel too!"

Reviewed on Jan 19, 2025

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $103 per night from Feb 2 to Feb 3
$103
includes taxes & fees
Feb 2 - Feb 3
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,712 reviews)
"👍"

Reviewed on Jan 17, 2025

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
The price is $110 per night from Feb 19 to Feb 20
$110
includes taxes & fees
Feb 19 - Feb 20
Stay at this 4-star 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 ...
8.6/10 Excellent! (2,797 reviews)
"The staff was friendly. Made sure my stay was comfortable. The room was decent for the price . The only downsize was the bathroom area. It’s more of a barn style and there really isn’t any privacy . There is a curtain to close off the view from the room to shower . The side door closes from closet ..."

Reviewed on Jan 16, 2025

Eurostars Magnificent Mile
Pendry Chicago
Pendry Chicago
4.5 out of 5
230 North Michigan Avenue, Chicago, IL
The price is $235 per night from Feb 3 to Feb 4
$235
includes taxes & fees
Feb 3 - Feb 4
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff ...
9.2/10 Wonderful! (1,004 reviews)
"Good and beverage extremely overpriced"

Reviewed on Jan 13, 2025

Pendry Chicago
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
The price is $101 per night from Jan 22 to Jan 23
$101
includes taxes & fees
Jan 22 - Jan 23
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! (1,662 reviews)
"Second time staying at this property. Close to the airport!"

Reviewed on Jan 20, 2025

Hampton Inn Chicago-O'Hare International Airport
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
The price is $116 per night from Feb 5 to Feb 6
$116
includes taxes & fees
Feb 5 - Feb 6
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! (2,562 reviews)
"Great place…"

Reviewed on Jan 16, 2025

citizenM Chicago Downtown
Holiday Inn Chicago Dwtn - The Mart, an IHG Hotel
Holiday Inn Chicago Dwtn - The Mart, an IHG Hotel
3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
The price is $141 per night from Jan 30 to Jan 31
$141
includes taxes & fees
Jan 30 - Jan 31
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,340 reviews)
"Real nice"

Reviewed on Jan 18, 2025

Holiday Inn Chicago Dwtn - The Mart, an IHG Hotel
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
The price is $193 per night from Jan 24 to Jan 25
$193
includes taxes & fees
Jan 24 - Jan 25
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,620 reviews)
"The Hotel got history and very easy to get public transportation"

Reviewed on Jan 18, 2025

Hilton Chicago
See all 4,979 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
2.5 out of 5
2951 Touhy Ave, Elk Grove Village, IL
The price is $73 per night from Jan 22 to Jan 23
$73
includes taxes & fees
Jan 22 - Jan 23
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 ...
7.8/10 Good! (1,064 reviews)
"The staff did such a great job of being friendly and professional."

Reviewed on Jan 18, 2025

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
The price is $91 per night from Feb 10 to Feb 11
$91
includes taxes & fees
Feb 10 - Feb 11
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 ...
6.6/10 (1,005 reviews)
"Overall Good,would like to stay there again"

Reviewed on Jan 17, 2025

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
The price is $101 per night from Jan 22 to Jan 23
$101
includes taxes & fees
Jan 22 - Jan 23
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! (1,662 reviews)
"Second time staying at this property. Close to the airport!"

Reviewed on Jan 20, 2025

Hampton Inn Chicago-O'Hare International Airport
Holiday Inn Chicago O'Hare Area, an IHG Hotel
Holiday Inn Chicago O'Hare Area, an IHG Hotel
3 out of 5
5615 North Cumberland Avenue, Chicago, IL
The price is $112 per night from Jan 26 to Jan 27
$112
includes taxes & fees
Jan 26 - Jan 27
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! (1,003 reviews)
"The bar"

Reviewed on Jan 15, 2025

Holiday Inn Chicago O'Hare Area, an IHG Hotel
Loews Chicago O'Hare Hotel
Loews Chicago O'Hare Hotel
4.5 out of 5
5300 N River Rd, Rosemont, IL
The price is $158 per night from Jan 24 to Jan 25
$158
includes taxes & fees
Jan 24 - Jan 25
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 ...
9.2/10 Wonderful! (1,693 reviews)
"Great location. Restaurant inside hotel and 2 restaurants in parking lot area to walk to."

Reviewed on Jan 16, 2025

Loews Chicago O'Hare Hotel
Carlton Inn Midway
Carlton Inn Midway
2 out of 5
4944 S Archer Ave, Chicago, IL
The price is $123 per night from Jan 22 to Jan 23
$123
includes taxes & fees
Jan 22 - Jan 23
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 ...
6.6/10 (1,002 reviews)
"The breakfast was surprisingly tasty hash browns, scrambled eggs, sausage patties.they also have cereal, bagels and oh and apple juice . I’ll be back!"

Reviewed on Jan 16, 2025

Carlton Inn Midway
See all 4,979 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.