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 $89

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

Frontier Airlines
Wed, Sep 16 - Mon, Sep 28
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$89 Roundtrip, found 3 days ago
$89
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Sep 28, priced at $89 found 3 days ago
Frontier Airlines
Tue, Aug 25 - Wed, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Aug 25 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Aug 26, priced at $98 found 2 days ago
Frontier Airlines
Tue, Jun 9 - Wed, Jun 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jun 10, priced at $98 found 1 day ago
Frontier Airlines
Mon, Sep 14 - Tue, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$99 Roundtrip, found 3 days ago
$99
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Sep 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $99 found 3 days ago
Frontier Airlines
Sat, Aug 29 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$100 Roundtrip, found 4 days ago
$100
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 9, priced at $100 found 4 days ago
Frontier Airlines
Tue, Jul 7 - Tue, Jul 21
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jul 7 from George Bush Intercontinental to O'Hare Intl., returning Tue, Jul 21, priced at $110 found 2 days ago
Frontier Airlines
Fri, Aug 28 - Thu, Sep 3
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 5 days ago
$124
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Aug 28 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Thu, Sep 3, priced at $124 found 5 days ago
Bargain Flight
Tue, Sep 15 - Tue, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$177 Roundtrip, found 11 hours ago
$177
Roundtrip
found 11 hours ago
Select Bargain Flight flight, departing Tue, Sep 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $177 found 11 hours ago
JetBlue Airways
Wed, Sep 9 - Tue, Sep 15
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 20 hours ago
$189
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Wed, Sep 9 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Tue, Sep 15, priced at $189 found 20 hours ago
American Airlines
Wed, Aug 19 - Wed, Aug 26
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 19 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Wed, Aug 26, priced at $189 found 1 day ago
Delta
Tue, Sep 15 - Tue, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 11 hours ago
$197
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Sep 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $197 found 11 hours ago
Delta
Wed, Aug 5 - Tue, Aug 18
IAH
George Bush Intercontinental
MDW
Midway Intl.
$209 Roundtrip, found 10 hours ago
$209
Roundtrip
found 10 hours ago
Select Delta flight, departing Wed, Aug 5 from George Bush Intercontinental to Midway Intl., returning Tue, Aug 18, priced at $209 found 10 hours ago
Delta
Tue, Sep 1 - Tue, Sep 8
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 1 from Fort Lauderdale - Hollywood Intl. to Midway Intl., returning Tue, Sep 8, priced at $217 found 1 day ago
American Airlines
Tue, Jun 23 - Sat, Jun 27
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$276 Roundtrip, found 1 day ago
$276
Roundtrip
found 1 day 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 1 day ago
American Airlines
Fri, May 29 - Sat, Aug 1
IAH
George Bush Intercontinental
RFD
Greater Rockford
$329 Roundtrip, found 1 day ago
$329
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, May 29 from George Bush Intercontinental to Greater Rockford, returning Sat, Aug 1, priced at $329 found 1 day ago
Alaska Airlines
Thu, Jul 9 - Mon, Jul 13
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$827 Roundtrip, found 3 hours ago
$827
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Thu, Jul 9 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Mon, Jul 13, priced at $827 found 3 hours 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 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 $89, 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 $89 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$89

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! (10,128 reviews)
"Bring earplugs, people love driving down Michigan avenue blasting music loudly"

Reviewed on May 22, 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! (4,210 reviews)
"The hotel was marvelous. The breakfasts were amazing. Anything you could think of was there. The rooftop bar is definitely worth visiting."

Reviewed on May 22, 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! (2,712 reviews)
"Na"

Reviewed on May 21, 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! (1,452 reviews)
"Valet parking was terrible and I should have received a $30 discount off of the valet parking per my reservation and they charged me the full amount. Also waited over 30mins for valet to get my car"

Reviewed on May 21, 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! (5,187 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! (2,324 reviews)
"The location is very good, but the hotel needs to make some improvements. First, when you enter, there is a strong smell of humidity, which I imagine is coming from the carpet. The same smell was noticeable in the hallways and in the room. In the room, I found that the sink was clogged, and the shower ..."

Reviewed on May 21, 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! (2,164 reviews)
"Amazing staff. Clean rooms!"

Reviewed on May 21, 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! (3,033 reviews)
"The staff was lovely as always. The room was nice and clean."

Reviewed on May 22, 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! (1,669 reviews)
"Everything was good until the large frame of Chicago city fell on the next day out of no where. Apart from that, it was good. Be careful, those frames are not properly hanged."

Reviewed on May 22, 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! (1,439 reviews)
"The room was clean and I love the late check out"

Reviewed on May 21, 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! (2,299 reviews)
"We couldn’t sleep because it was so noisy being close to the highway"

Reviewed on May 21, 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! (1,001 reviews)
"Staff is nice. Hotel needs a little upgrade. Breakfast was amazing!!"

Reviewed on May 20, 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! (2,066 reviews)
"Very clean and the staff were very kind and respectful. In town for a convention and the room was spacious and very relaxing."

Reviewed on May 20, 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 (1,002 reviews)
"Good"

Reviewed on May 21, 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.