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Chicago

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Chicago Flights as Low as $103

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

Frontier Airlines
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$103 Roundtrip, found 2 hours ago
$103
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $103 found 2 hours ago
Frontier Airlines
Wed, Dec 2 - Tue, Dec 15
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$118 Roundtrip, found 3 hours ago
$118
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 15, priced at $118 found 3 hours ago
Frontier Airlines
Thu, Nov 19 - Tue, Dec 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 2 hours ago
$118
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Nov 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 1, priced at $118 found 2 hours ago
Frontier Airlines
Fri, Dec 4 - Sun, Dec 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$123 Roundtrip, found 3 hours ago
$123
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Dec 6, priced at $123 found 3 hours ago
Frontier Airlines
Tue, Jan 19 - Wed, Feb 10
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$128 Roundtrip, found 3 hours ago
$128
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, Jan 19 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Feb 10, priced at $128 found 3 hours ago
Frontier Airlines
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 2 hours ago
$132
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $132 found 2 hours ago
Frontier Airlines
Sat, Feb 27 - Tue, Mar 2
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$140 Roundtrip, just found
$140
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Feb 27 from George Bush Intercontinental to O'Hare Intl., returning Tue, Mar 2, priced at $140 just found
Bargain Flight
Tue, Nov 3 - Tue, Nov 17
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Nov 3 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Nov 17, priced at $187 found 1 day ago
American Airlines
Sat, Dec 5 - Sat, Dec 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$192 Roundtrip, found 3 hours ago
$192
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sat, Dec 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 5, priced at $192 found 3 hours ago
Delta
Sat, Dec 5 - Sat, Dec 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$192 Roundtrip, found 3 hours ago
$192
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Dec 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 5, priced at $192 found 3 hours ago
Southwest Airlines
Wed, Dec 2 - Tue, Dec 15
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$197 Roundtrip, found 3 hours ago
$197
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 15, priced at $197 found 3 hours ago
Southwest Airlines
Tue, Dec 8 - Tue, Dec 15
DAL
Love Field
MDW
Midway Intl.
$199 Roundtrip, just found
$199
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Dec 8 from Love Field to Midway Intl., returning Tue, Dec 15, priced at $199 just found
Frontier Airlines
Tue, Nov 24 - Tue, Dec 1
IAH
George Bush Intercontinental
MDW
Midway Intl.
$225 Roundtrip, found 3 hours ago
$225
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, Nov 24 from George Bush Intercontinental to Midway Intl., returning Tue, Dec 1, priced at $225 found 3 hours ago
JetBlue Airways
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 2 hours ago
$257
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 $257 found 2 hours ago
Delta
Tue, Dec 1 - Mon, Dec 14
DAL
Love Field
ORD
O'Hare Intl.
$258 Roundtrip, just found
$258
Roundtrip
just found
Select Delta flight, departing Tue, Dec 1 from Love Field to O'Hare Intl., returning Mon, Dec 14, priced at $258 just found
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Dec 20 - Sat, Dec 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$468 Roundtrip, found 1 day ago
$468
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Dec 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 26, priced at $468 found 1 day 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 $103, 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 $103 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$103

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! (10,080 reviews)
"I stayed on Halloween and the room next to me was so incredibly loud and I know it was Halloween but it was ridiculous. Their party lasted until 1:00 in the morning and it sounded like it was in my room ."

Reviewed on Nov 1, 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! (2,632 reviews)
"Le déjeuner était vraiment très bien. Buffet diversifié"

Reviewed on Nov 1, 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 ...
8.6/10 Excellent! (2,184 reviews)
"Everything was great, the staff were very helpful and friendly"

Reviewed on Nov 1, 2026

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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! (2,509 reviews)
"We had a wonderful time!"

Reviewed on Nov 1, 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 ...
8.6/10 Excellent! (3,506 reviews)
"Charged way too much for a keal I thought was complimentary and a 25 resort charge that didn't quite make sense ..I wasn't staying at a resort to my knowledge."

Reviewed on Nov 1, 2026

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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! (1,012 reviews)
"Air conditioning worked poorly. Room never cooled down below 75 degrees. Room safe did not work. Room is sparse and lacked comfort. Quite a let down from other Marriott tribute properties."

Reviewed on Nov 1, 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! (3,670 reviews)
"Clean room and great staff."

Reviewed on Oct 31, 2026

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The Royal Sonesta Chicago Downtown
See all 5,558 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 ...
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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 ...
7.6/10 Good! (1,896 reviews)
"Really nice location and room. The hotel was getting renovated so no workout room at the hotel but they were able to use one across the parking lot which was great. They definitely are on the right track and were very accommodating. Would recommend"

Reviewed on Nov 1, 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 ...
9.4/10 Exceptional! (2,412 reviews)
"This is very good location and the staff is wonderful. I love it bc it’s very accessible and quiet"

Reviewed on Nov 1, 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! (2,278 reviews)
"Too expensive for the room and amenities. Won’t stay again. Staff wonderful, but park and staying not worth it"

Reviewed on Nov 1, 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 ...
5.8/10 (1,003 reviews)
"Bathroom was dirty, there was a hole behind bathroom door from door knob. Towels looked clean, but were stained yellow. Yuck! T.v didn’t work, wires were all over the floor. Wardrobe shelving was rickety and lopsided. There was other furniture and appliances missing. Accommodations were not satisfactory. ..."

Reviewed on Oct 31, 2026

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Carlton Inn Midway
See all 5,558 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.