Search Cheap Flights to
Chicago

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Chicago Flights as Low as $77

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

Frontier Airlines
Wed, Sep 16 - Tue, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$77 Roundtrip, found 5 hours ago
$77
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $77 found 5 hours ago
Frontier Airlines
Tue, Sep 15 - Tue, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$87 Roundtrip, found 1 day ago
$87
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Sep 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $87 found 1 day ago
Frontier Airlines
Tue, Aug 25 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$88 Roundtrip, found 5 hours ago
$88
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Aug 25 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 9, priced at $88 found 5 hours ago
Frontier Airlines
Tue, Aug 4 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 5 hours ago
$88
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Aug 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 25, priced at $88 found 5 hours ago
Frontier Airlines
Sat, Aug 29 - Thu, Sep 17
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$89 Roundtrip, found 18 hours ago
$89
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Sat, Aug 29 from George Bush Intercontinental to O'Hare Intl., returning Thu, Sep 17, priced at $89 found 18 hours ago
American Airlines
Tue, Aug 11 - Tue, Aug 18
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$189 Roundtrip, found 2 hours ago
$189
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Aug 11 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 18, priced at $189 found 2 hours ago
United
Tue, Aug 11 - Tue, Aug 18
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$189 Roundtrip, found 2 hours ago
$189
Roundtrip
found 2 hours ago
Select United flight, departing Tue, Aug 11 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 18, priced at $189 found 2 hours ago
Frontier Airlines
Tue, Oct 27 - Tue, Nov 17
AUS
Austin-Bergstrom Intl.
ORD
O'Hare Intl.
$200 Roundtrip, found 2 days ago
$200
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Oct 27 from Austin-Bergstrom Intl. to O'Hare Intl., returning Tue, Nov 17, priced at $200 found 2 days ago
Frontier Airlines
Tue, Oct 20 - Tue, Nov 10
IAH
George Bush Intercontinental
MDW
Midway Intl.
$200 Roundtrip, found 5 days ago
$200
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Oct 20 from George Bush Intercontinental to Midway Intl., returning Tue, Nov 10, priced at $200 found 5 days ago
Delta
Wed, Aug 5 - Mon, Aug 17
IAH
George Bush Intercontinental
MDW
Midway Intl.
$208 Roundtrip, found 5 days ago
$208
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Aug 5 from George Bush Intercontinental to Midway Intl., returning Mon, Aug 17, priced at $208 found 5 days ago
Frontier Airlines
Tue, Jun 9 - Fri, Jun 12
AUS
Austin-Bergstrom Intl.
MDW
Midway Intl.
$246 Roundtrip, found 5 days ago
$246
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Austin-Bergstrom Intl. to Midway Intl., returning Fri, Jun 12, priced at $246 found 5 days ago
American Airlines
Tue, Jun 23 - Sat, Jun 27
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$276 Roundtrip, found 2 hours ago
$276
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Jun 23 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sat, Jun 27, priced at $276 found 2 hours ago
JetBlue Airways
Tue, Aug 4 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$297 Roundtrip, found 5 hours ago
$297
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 25, priced at $297 found 5 hours ago
American Airlines
Fri, Sep 4 - Sat, Sep 5
AUS
Austin-Bergstrom Intl.
RFD
Greater Rockford
$335 Roundtrip, found 6 days ago
$335
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Sep 4 from Austin-Bergstrom Intl. to Greater Rockford, returning Sat, Sep 5, priced at $335 found 6 days ago
American Airlines
Fri, May 29 - Sat, Aug 1
IAH
George Bush Intercontinental
RFD
Greater Rockford
$335 Roundtrip, found 6 days ago
$335
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, May 29 from George Bush Intercontinental to Greater Rockford, returning Sat, Aug 1, priced at $335 found 6 days ago
Alaska Airlines
Sat, Jun 6 - Mon, Jun 8
AUS
Austin-Bergstrom Intl.
ORD
O'Hare Intl.
$535 Roundtrip, found 6 days ago
$535
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Sat, Jun 6 from Austin-Bergstrom Intl. to O'Hare Intl., returning Mon, Jun 8, priced at $535 found 6 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 September, 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 $77, 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 $77 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$77

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! (10,167 reviews)
"I had an amazing view of Lake Michigan and the area but unfortunately Michigan Ave is very noisy at all times of the day and night. In addition, there were no black out shades and due to the rooms facing East, the sunrise was bright and early. I had to buy a sleeping mask just to sleep to 7am. The ..."

Reviewed on May 19, 2026

Get rates
Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,192 reviews)
"New amenities, awesome breakfast, great location. Pleasently surprised, especially by the quality of the breakfast."

Reviewed on May 19, 2026

Get rates
Hotel Riu Plaza Chicago
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (2,706 reviews)
"The room was clean but pretty basic. It was good overall but we did have an issue with the a/c switching off in the middle of the night. Unfortunately the hotel didn’t have any fans to remedy that situation. Other than that we had a very enjoyable stay. The location is great!"

Reviewed on May 19, 2026

Get rates
Hotel Felix River North/Magnificent Mile
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 ...
7.8/10 Good! (1,438 reviews)
"It was very clean and met standards"

Reviewed on May 20, 2026

Get rates
The Chicago Hotel Collection - Magnificent Mile
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 ...
8.8/10 Excellent! (5,182 reviews)
"Very pleased with my stay. Room was a little small but otherwise very good. Clean and well maintained. Location is excellent."

Reviewed on May 19, 2026

Get rates
River Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (2,323 reviews)
"Okay"

Reviewed on May 19, 2026

Get rates
Holiday Inn Chicago Dwtn - The Mart by IHG
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (2,163 reviews)
"Great breakfast"

Reviewed on May 20, 2026

Get rates
Fairmont Chicago at Millennium Park
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (3,022 reviews)
"My wife and I expected and paid for what was advertised as a larger room with a queen bed and desk. There was no room to walk around the bed or "sit" at the desk, which was maybe a foot wide. The room, itself, was not all that clean, and the toilet was very close to the bed. I might have managed ..."

Reviewed on May 20, 2026

Get rates
Freehand Chicago
See all 5,570 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 ...
7.6/10 Good! (1,672 reviews)
"Room was clean , free was breakfast was decent , staff was nice"

Reviewed on May 19, 2026

Get rates
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! (1,436 reviews)
"Breakfast was awesome fresh coffee and also the pool was definitely relaxing after working in the kitchen at aggtuccis in Peoria il the shower was really nice to and it was overall the best stay in a hotel I have ever been in thanks again keegan Johnston from Peoria il"

Reviewed on May 19, 2026

Get rates
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 ...
9.2/10 Wonderful! (2,292 reviews)
"Great airport shuttle. Super friendly staff"

Reviewed on May 20, 2026

Get rates
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 ...
8.2/10 Very Good! (1,002 reviews)
"NA"

Reviewed on May 14, 2026

Get rates
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! (2,064 reviews)
"The room was very clean. The staff were nice. The food was expensive and bland."

Reviewed on May 17, 2026

Get rates
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 ...
6.2/10 (1,000 reviews)
"Breakfast wasnt stocked very well, 1st come 1st serve and when its gone its gone it felt like. It didnt taste good either. Sheets were strained, and the bathroom is super tiny, no counter space. Beds were decent besides the sheets. Showers had awful water pressure. Staff was polite and courteous. ..."

Reviewed on May 17, 2026

Get rates
Carlton Inn Midway
See all 5,570 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.