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 $56

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

Frontier Airlines
Tue, Apr 21 - Wed, Apr 22
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$56 Roundtrip, found 1 day ago
$56
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Apr 21 from George Bush Intercontinental to O'Hare Intl., returning Wed, Apr 22, priced at $56 found 1 day ago
Frontier Airlines
Wed, Mar 11 - Wed, Mar 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$66 Roundtrip, found 4 hours ago
$66
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Mar 11 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 11, priced at $66 found 4 hours ago
Frontier Airlines
Wed, Mar 25 - Mon, Mar 30
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$67 Roundtrip, found 23 hours ago
$67
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Wed, Mar 25 from Harry Reid Intl. to O'Hare Intl., returning Mon, Mar 30, priced at $67 found 23 hours ago
Spirit Airlines
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$74 Roundtrip, found 3 days ago
$74
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $74 found 3 days ago
Frontier Airlines
Fri, Feb 27 - Mon, Mar 9
IAH
George Bush Intercontinental
MDW
Midway Intl.
$85 Roundtrip, found 1 day ago
$85
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Feb 27 from George Bush Intercontinental to Midway Intl., returning Mon, Mar 9, priced at $85 found 1 day ago
Frontier Airlines
Tue, May 5 - Sat, May 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 8 hours ago
$88
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, May 5 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 9, priced at $88 found 8 hours ago
United
Sat, Jul 4 - Sat, Jul 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jul 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Jul 4, priced at $99 found 1 day ago
Frontier Airlines
Tue, Mar 10 - Wed, Mar 11
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$100 Roundtrip, found 8 hours ago
$100
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, Mar 10 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Mar 11, priced at $100 found 8 hours ago
Delta
Sat, Jul 4 - Sat, Jul 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$131 Roundtrip, found 1 day ago
$131
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jul 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Jul 4, priced at $131 found 1 day ago
American Airlines
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $147 found 1 day ago
American Airlines
Mon, Apr 27 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$176 Roundtrip, found 8 hours ago
$176
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Mon, Apr 27 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, May 1, priced at $176 found 8 hours ago
Frontier Airlines
Fri, Apr 10 - Fri, Apr 17
LAX
Los Angeles Intl.
MDW
Midway Intl.
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Apr 10 from Los Angeles Intl. to Midway Intl., returning Fri, Apr 17, priced at $206 found 1 day ago
Delta
Wed, May 20 - Sat, Jun 13
LAS
Harry Reid Intl.
MDW
Midway Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 20 from Harry Reid Intl. to Midway Intl., returning Sat, Jun 13, priced at $237 found 1 day ago
American Airlines
Tue, Mar 17 - Wed, Mar 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 17 from Los Angeles Intl. to Greater Rockford, returning Wed, Mar 25, priced at $242 found 1 day ago
American Airlines
Sat, Mar 7 - Tue, Mar 10
IAH
George Bush Intercontinental
RFD
Greater Rockford
$270 Roundtrip, found 1 day ago
$270
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Mar 7 from George Bush Intercontinental to Greater Rockford, returning Tue, Mar 10, priced at $270 found 1 day ago
American Airlines
Fri, Feb 20 - Sat, Feb 21
LAS
Harry Reid Intl.
RFD
Greater Rockford
$403 Roundtrip, found 6 days ago
$403
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Feb 20 from Harry Reid Intl. to Greater Rockford, returning Sat, Feb 21, priced at $403 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 April, 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 $56, 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 $56 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$55

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! (9,867 reviews)
Great location, beautiful historic hotel with clean, updated rooms.

Reviewed on Feb 11, 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 ...
9.2/10 Wonderful! (3,337 reviews)
Best location, breakfast is excellent

Reviewed on Feb 13, 2026

Get rates
Hotel Riu Plaza Chicago
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 ...
8.4/10 Very Good! (2,617 reviews)
It was great

Reviewed on Feb 12, 2026

Get rates
Hilton Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.2/10 Very Good! (2,202 reviews)
Food at sports bar was great along with the service. Bedding was top notch, room clean& nice TV

Reviewed on Feb 9, 2026

Get rates
Hilton Chicago O'Hare Airport
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
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.4/10 Very Good! (5,668 reviews)
Great room, breakfast and the staff was very courteous.

Reviewed on Feb 15, 2026

Get rates
Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (3,787 reviews)
Room was OK. Pool was closed so I was very upset.

Reviewed on Feb 10, 2026

Get rates
Hilton Chicago/Magnificent Mile Suites
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (3,070 reviews)
It was a nice time. Ill be bringing my dog next time

Reviewed on Feb 13, 2026

Get rates
Aloft Chicago Mag Mile
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (2,286 reviews)
Clean room, nice size. Housekeeping staff in particular were very nice and helpful. No coffee maker in the room, hence 4 vs 5 stars.

Reviewed on Feb 10, 2026

Get rates
Palmer House a Hilton Hotel
See all 5,631 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! (1,611 reviews)
It is very affordable and all the amenities are decent. They have free parking facilities and airport drop off facility

Reviewed on Feb 12, 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 ...
7.2/10 Good! (1,265 reviews)
Clean room Excellent staff

Reviewed on Feb 12, 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! (2,217 reviews)
Room was nice, clean and comfortable! Friendly staff!!!

Reviewed on Feb 14, 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 ...
8/10 Very Good! (1,002 reviews)
The staff handled our late arrival with professional attitude. The room was clean, and as quiet as you can expect that close to the Kennedy and O'Hare. I like it, and I plan to go back when I need a place near the airport.

Reviewed on Feb 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! (1,954 reviews)
It was great

Reviewed on Feb 13, 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)
Clean room. Professional and courteous staff

Reviewed on Feb 13, 2026

Get rates
Carlton Inn Midway
See all 5,631 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.