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Chicago

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Chicago Flights as Low as $43

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

Frontier Airlines
Wed, Mar 12 - Wed, Mar 12
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$43 Roundtrip, found 4 days ago
$43
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Mar 12 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Mar 12, priced at $43 found 4 days ago
Frontier Airlines
Tue, Mar 11 - Wed, Mar 12
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$48 Roundtrip, found 4 days ago
$48
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Mar 11 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Mar 12, priced at $48 found 4 days ago
Frontier Airlines
Tue, Mar 18 - Tue, Mar 25
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$48 Roundtrip, found 2 days ago
$48
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Mar 18 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Mar 25, priced at $48 found 2 days ago
Frontier Airlines
Wed, Mar 26 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$48 Roundtrip, found 3 days ago
$48
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Mar 26 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $48 found 3 days ago
Spirit Airlines
Wed, Apr 2 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$48 Roundtrip, found 4 days ago
$48
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Apr 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $48 found 4 days ago
Frontier Airlines
Thu, Mar 20 - Wed, Mar 26
ONT
Los Angeles - Ontario Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 3 days ago
$120
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Mar 20 from Los Angeles - Ontario Intl. to O'Hare Intl., returning Wed, Mar 26, priced at $120 found 3 days ago
Frontier Airlines
Sat, Mar 1 - Thu, Mar 6
ONT
Los Angeles - Ontario Intl.
MDW
Midway Intl.
$121 Roundtrip, found 6 days ago
$121
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Mar 1 from Los Angeles - Ontario Intl. to Midway Intl., returning Thu, Mar 6, priced at $121 found 6 days ago
Delta
Wed, Apr 2 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 4 days ago
$134
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Apr 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $134 found 4 days ago
United
Wed, Apr 2 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$139 Roundtrip, found 4 days ago
$139
Roundtrip
found 4 days ago
Select United flight, departing Wed, Apr 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $139 found 4 days ago
American Airlines
Tue, Apr 22 - Tue, Apr 22
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$142 Roundtrip, found 10 hours ago
$142
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Apr 22 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Apr 22, priced at $142 found 10 hours ago
Delta
Sat, Mar 8 - Tue, Mar 11
DAL
Love Field
ORD
O'Hare Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Mar 8 from Love Field to O'Hare Intl., returning Tue, Mar 11, priced at $217 found 1 day ago
Delta
Sat, Apr 12 - Tue, Apr 15
DAL
Love Field
MDW
Midway Intl.
$218 Roundtrip, found 6 days ago
$218
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Apr 12 from Love Field to Midway Intl., returning Tue, Apr 15, priced at $218 found 6 days ago
Contour Airlines
Fri, Mar 21 - Mon, Mar 24
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$230 Roundtrip, found 2 days ago
$230
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Fri, Mar 21 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Mar 24, priced at $230 found 2 days ago
American Airlines
Wed, Oct 15 - Mon, Oct 20
ICT
Wichita Dwight D. Eisenhower National
ORD
O'Hare Intl.
$268 Roundtrip, found 2 days ago
$268
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Oct 15 from Wichita Dwight D. Eisenhower National to O'Hare Intl., returning Mon, Oct 20, priced at $268 found 2 days ago
Delta
Tue, Feb 25 - Tue, Mar 4
ICT
Wichita Dwight D. Eisenhower National
MDW
Midway Intl.
$305 Roundtrip, found 1 day ago
$305
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Feb 25 from Wichita Dwight D. Eisenhower National to Midway Intl., returning Tue, Mar 4, priced at $305 found 1 day ago
JetBlue Airways
Sat, Mar 8 - Tue, Mar 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$309 Roundtrip, found 4 days ago
$309
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sat, Mar 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Mar 11, priced at $309 found 4 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 March, 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 $43, 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 $43 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$42

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 $115 per night from Feb 23 to Feb 24
$115
includes taxes & fees
Feb 23 - Feb 24
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! (8,508 reviews)
"The city"

Reviewed on Feb 18, 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 27 to Feb 28
$103
includes taxes & fees
Feb 27 - Feb 28
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! (3,799 reviews)
"Located across the street from the River walkway and a couple of blocks from shopping, restaurants and Starbucks Reserve."

Reviewed on Feb 20, 2025

River Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
The price is $163 per night from Feb 23 to Feb 24
$163
includes taxes & fees
Feb 23 - Feb 24
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and ...
9.6/10 Exceptional! (1,673 reviews)
"It was a great experience"

Reviewed on Feb 20, 2025

L7 Chicago by LOTTE
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
The price is $204 per night from Feb 28 to Mar 1
$204
includes taxes & fees
Feb 28 - Mar 1
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! (1,658 reviews)
"Beautiful hotel in the perfect area"

Reviewed on Feb 18, 2025

Hilton Chicago
Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
The price is $124 per night from Feb 23 to Feb 24
$124
includes taxes & fees
Feb 23 - Feb 24
Book a stay at this eco-certified hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,302 reviews)
"The room was beautiful"

Reviewed on Feb 18, 2025

Hyatt Regency O'Hare Chicago
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
The price is $117 per night from Feb 23 to Feb 24
$117
includes taxes & fees
Feb 23 - Feb 24
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! (2,694 reviews)
Chicago hotel experience
"The hotel is meant for people who are comfortable with technology and do not mind having an average space.Technology was a major focal points in the room decor. A tablet controls everything from the lighting up until the television. The restroom gets the job done. The best part of the hotel is the ..."

Reviewed on Feb 20, 2025

citizenM Chicago Downtown
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
The price is $231 per night from Mar 21 to Mar 22
$231
includes taxes & fees
Mar 21 - Mar 22
Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (3,203 reviews)
"Amazing stay"

Reviewed on Feb 17, 2025

Hyatt Regency Chicago
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
4.5 out of 5
200 North Columbus Drive, Chicago, IL
The price is $229 per night from Feb 22 to Feb 23
$229
includes taxes & fees
Feb 22 - Feb 23
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,635 reviews)
"Muy buena atención excelente servicio"

Reviewed on Feb 21, 2025

Fairmont Chicago at Millennium Park
See all 5,028 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 $79 per night from Feb 23 to Feb 24
$79
includes taxes & fees
Feb 23 - Feb 24
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! (1,082 reviews)
"Sraff was great. Property bed and decor is worn out."

Reviewed on Feb 19, 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 $94 per night from Mar 3 to Mar 4
$94
includes taxes & fees
Mar 3 - Mar 4
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 (1,000 reviews)
"The first room I was given it was cold so I went to the front desk explain my issues and was given a NEW room with no problem the washing machines and dryers DOESNT WORK, I wasn't refunded the money I lost. the breakfast was a nice. They severed eggs,biscuit, gravy waffles, oatmeal, cold cereal drink ..."

Reviewed on Feb 15, 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 Feb 23 to Feb 24
$101
includes taxes & fees
Feb 23 - Feb 24
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! (1,737 reviews)
"Perfect for a spending a night before getting on an early morning flight at OHare. Free Shuttle free parking. Low stress. Clean rooms. Nice facility."

Reviewed on Feb 19, 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 $107 per night from Mar 9 to Mar 10
$107
includes taxes & fees
Mar 9 - Mar 10
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! (1,004 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 Feb 22 to Feb 23
$158
includes taxes & fees
Feb 22 - Feb 23
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! (1,747 reviews)
"The staff was very friendly. Our room was clean and spacious :)"

Reviewed on Feb 20, 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 $140 per night from Feb 22 to Feb 23
$140
includes taxes & fees
Feb 22 - Feb 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 (1,001 reviews)
"Love the free airport transport. This is a MOTEL. I thought it was a hotel. Scary part of town. Lots of noises from cleaning/laundry/maintenance , as well as surrounding area."

Reviewed on Feb 11, 2025

Carlton Inn Midway
See all 5,028 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.