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Chicago

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Chicago Flights as Low as $58

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

Frontier Airlines
Wed, Feb 26 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Feb 26 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Mar 4, priced at $58 found 1 day ago
Frontier Airlines
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $63 found 1 day ago
Frontier Airlines
Tue, Feb 18 - Tue, Feb 25
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Feb 18 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Feb 25, priced at $63 found 1 day ago
Frontier Airlines
Wed, Feb 19 - Tue, Feb 25
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 3 days ago
$68
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Feb 19 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Feb 25, priced at $68 found 3 days ago
Frontier Airlines
Wed, Feb 19 - Sat, Mar 1
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 3 days ago
$73
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Feb 19 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Mar 1, priced at $73 found 3 days ago
Frontier Airlines
Sat, Feb 22 - Tue, Feb 25
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$78 Roundtrip, found 3 days ago
$78
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Feb 22 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Feb 25, priced at $78 found 3 days ago
Frontier Airlines
Sat, Feb 22 - Sat, Mar 1
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 3 days ago
$83
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Feb 22 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Mar 1, priced at $83 found 3 days ago
Spirit Airlines
Wed, Jan 8 - Wed, Jan 8
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 4 days ago
$88
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Jan 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jan 8, priced at $88 found 4 days ago
Frontier Airlines
Mon, Jan 13 - Thu, Jan 16
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$118 Roundtrip, found 3 days ago
$118
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Jan 13 from Dallas-Fort Worth Intl. to Midway Intl., returning Thu, Jan 16, priced at $118 found 3 days ago
Delta
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $132 found 1 day ago
American Airlines
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $132 found 1 day ago
United
Wed, Jan 22 - Tue, Jan 28
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 10 hours ago
$137
Roundtrip
found 10 hours ago
Select United flight, departing Wed, Jan 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jan 28, priced at $137 found 10 hours ago
Contour Airlines
Wed, Feb 12 - Thu, Feb 13
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 Wed, Feb 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Feb 13, priced at $189 found 2 days ago
Delta
Tue, Feb 4 - Tue, Feb 4
DAL
Love Field
ORD
O'Hare Intl.
$193 Roundtrip, found 4 days ago
$193
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Feb 4 from Love Field to O'Hare Intl., returning Tue, Feb 4, priced at $193 found 4 days ago
Delta
Wed, Jan 29 - Fri, Jan 31
DAL
Love Field
MDW
Midway Intl.
$206 Roundtrip, found 6 days ago
$206
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 29 from Love Field to Midway Intl., returning Fri, Jan 31, priced at $206 found 6 days ago
JetBlue Airways
Wed, Jan 22 - Mon, Jan 27
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$262 Roundtrip, found 2 days ago
$262
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Jan 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Jan 27, priced at $262 found 2 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 February, 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 $58, 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 $58 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 $143 per night from Dec 22 to Dec 23
$143
includes taxes & fees
Dec 22 - Dec 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! (8,261 reviews)
"Beautiful hotel with a great location"

Reviewed on Dec 19, 2024

Congress Plaza Hotel
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
The price is $125 per night from Jan 12 to Jan 13
$125
includes taxes & fees
Jan 12 - Jan 13, 2025
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. ...
8.2/10 Very Good! (3,351 reviews)
"Everything was great. Hotel, happy hour Everyday. Complimentary breakfast. Wow!"

Reviewed on Dec 19, 2024

Embassy Suites by Hilton Chicago Downtown River North
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
The price is $193 per night from Jan 10 to Jan 11
$193
includes taxes & fees
Jan 10 - Jan 11, 2025
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 ...
9/10 Wonderful! (3,118 reviews)
"Esta muy bien ubicado,cerca de casi todos los puntos turisticos,muy tranquilo ,limpio ,el unico detalle q le note el agua de la ducha no tiene fuerza ,pero no es nada como para no volver ,es solo un detalle.por el resto regresaria mil veces."

Reviewed on Dec 20, 2024

Hyatt Regency Chicago
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $109 per night from Jan 20 to Jan 21
$109
includes taxes & fees
Jan 20 - Jan 21, 2025
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! (3,620 reviews)
"This hotel is great! The staff helped us check in early and provided us with a river view room. My friend and I were both very happy^^ Although it’s close to the busy road, the room is not noisy. The location of the hotel is also very good, making our travel convenient."

Reviewed on Dec 17, 2024

River Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
The price is $131 per night from Dec 22 to Dec 23
$131
includes taxes & fees
Dec 22 - Dec 23
Stay at this 4-star family-friendly hotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and in-room massages. Our guests praise the ...
8/10 Very Good! (2,797 reviews)
"Great location on Michigan Ave. Nice walk to area attractions, shopping and restaurants. Could use a little updating. Bed was not the best."

Reviewed on Dec 18, 2024

Warwick Allerton - Chicago
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
The price is $175 per night from Jan 5 to Jan 6
$175
includes taxes & fees
Jan 5 - Jan 6, 2025
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (1,249 reviews)
"This hotel never disappoints. City views are beautiful!"

Reviewed on Dec 18, 2024

L7 Chicago by LOTTE
W Chicago - Lakeshore
W Chicago - Lakeshore
4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
The price is $158 per night from Dec 26 to Dec 27
$158
includes taxes & fees
Dec 26 - Dec 27
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a health club. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,003 reviews)
Business travel
"Excellent accomodations"

Reviewed on Dec 18, 2024

W Chicago - Lakeshore
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
The price is $118 per night from Jan 13 to Jan 14
$118
includes taxes & fees
Jan 13 - Jan 14, 2025
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 ...
7.8/10 Good! (1,367 reviews)
"Great hotel, waking distance from a lot of shops and restaurants"

Reviewed on Dec 17, 2024

Hotel Felix River North/Magnificent Mile
See all 4,890 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 Dec 29 to Dec 30
$79
includes taxes & fees
Dec 29 - Dec 30
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! (1,036 reviews)
"Everything is good"

Reviewed on Dec 20, 2024

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 Dec 29 to Dec 30
$91
includes taxes & fees
Dec 29 - Dec 30
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 (1,002 reviews)
"Very friendly staff and very nice rooms."

Reviewed on Dec 20, 2024

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 $113 per night from Dec 22 to Dec 23
$113
includes taxes & fees
Dec 22 - Dec 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! (1,550 reviews)
"The food was good, the parking was very convenient, and the location was convenient too. The only thing I had a problem with was the showers. The glass sliding door only went one way, so you had to get in to set the temperature correctly. The door kept sliding open too, and it was really hard to ..."

Reviewed on Dec 19, 2024

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 $114 per night from Dec 23 to Dec 24
$114
includes taxes & fees
Dec 23 - Dec 24
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)
"Nice restaurant"

Reviewed on Dec 19, 2024

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 Dec 27 to Dec 28
$158
includes taxes & fees
Dec 27 - Dec 28
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! (1,673 reviews)
"Amazingly quiet for the area (not far from airport). Exceptionally comfortable King sized bed and pillows with amenities not that far from any floor. Would recommend for anyone looking to just get away."

Reviewed on Dec 19, 2024

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 Dec 22 to Dec 23
$140
includes taxes & fees
Dec 22 - Dec 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 (1,000 reviews)
Iffy
"The rooms do not look like what the pictures show on hotel.com. There are no dressers in the room and the bedding needs desperate attention. No mattress cover and covers are worn and as holes"

Reviewed on Nov 7, 2024

Carlton Inn Midway
See all 4,890 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.