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 $107

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

Frontier Airlines
Sat, Sep 5 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$107 Roundtrip, found 17 hours ago
$107
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 9, priced at $107 found 17 hours ago
Frontier Airlines
Sat, Sep 5 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$127 Roundtrip, found 1 hour ago
$127
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $127 found 1 hour ago
Frontier Airlines
Thu, Oct 15 - Wed, Oct 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 1 hour ago
$138
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Oct 15 from Los Angeles Intl. to O'Hare Intl., returning Wed, Oct 21, priced at $138 found 1 hour ago
Frontier Airlines
Sun, Sep 6 - Thu, Sep 10
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 10 hours ago
$171
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sun, Sep 6 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Sep 10, priced at $171 found 10 hours ago
Bargain Flight
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 17 hours ago
$172
Roundtrip
found 17 hours ago
Select Bargain Flight flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $172 found 17 hours ago
Frontier Airlines
Thu, Sep 10 - Sat, Sep 12
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$198 Roundtrip, found 17 hours ago
$198
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Sep 10 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Sep 12, priced at $198 found 17 hours ago
Delta
Fri, Nov 6 - Mon, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Nov 6 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 16, priced at $217 found 1 hour ago
American Airlines
Fri, Nov 6 - Mon, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Fri, Nov 6 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 16, priced at $217 found 1 hour ago
Southwest Airlines
Tue, Sep 22 - Tue, Sep 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$241 Roundtrip, found 8 hours ago
$241
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Tue, Sep 22 from Los Angeles Intl. to Midway Intl., returning Tue, Sep 29, priced at $241 found 8 hours ago
American Airlines
Wed, Sep 2 - Wed, Sep 16
LAX
Los Angeles Intl.
RFD
Greater Rockford
$300 Roundtrip, found 3 days ago
$300
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Greater Rockford, returning Wed, Sep 16, priced at $300 found 3 days ago
Alaska Airlines
Fri, Nov 6 - Mon, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$337 Roundtrip, found 1 hour ago
$337
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Fri, Nov 6 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 16, priced at $337 found 1 hour ago
American Airlines
Thu, Sep 10 - Sat, Sep 12
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$354 Roundtrip, found 1 hour ago
$354
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Sep 10 from Dallas-Fort Worth Intl. to Greater Rockford, returning Sat, Sep 12, priced at $354 found 1 hour ago
American Airlines
Fri, Sep 11 - Sun, Sep 13
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$367 Roundtrip, found 2 days ago
$367
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Sep 11 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sun, Sep 13, priced at $367 found 2 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Sep 21 - Sat, Sep 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$427 Roundtrip, found 1 hour ago
$427
Roundtrip
found 1 hour ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Sep 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 26, priced at $427 found 1 hour ago
JetBlue Airways
Mon, Sep 21 - Sat, Sep 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$431 Roundtrip, found 1 hour ago
$431
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Mon, Sep 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 26, priced at $431 found 1 hour ago
Sun Country Airlines
Wed, Nov 25 - Sat, Nov 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$443 Roundtrip, found 3 hours ago
$443
Roundtrip
found 3 hours ago
Select Sun Country Airlines flight, departing Wed, Nov 25 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Nov 28, priced at $443 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 $107, 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 $107 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$106

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 ...
Get rates
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (2,125 reviews)
"Staff were amazing! Extremely helpful and accommodating, let us check in about 5 hours early. Definitely recommend"

Reviewed on Aug 29, 2026

Get rates
The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (880 reviews)
"Check in can be slightly confusing however you get the hang of it quickly. It was close to many amenities, a train away or a longer walk. The loft was cleaning than most however there was still dust and some crumbs left behind. Over all we were pleased with our stay even though very pricey for 3 ..."

Reviewed on Aug 29, 2026

Get rates
Kasa Magnificent Mile Chicago
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
Get rates
Hampton Inn Chicago Downtown/Magnificent Mile
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 ...
8.6/10 Excellent! (3,102 reviews)
"The hotel was exceptionally beautifully and the staff were so friendly and helpful. We were there for the BTS concert and the hotel went out of their way to make the space welcoming to Army (fans) by setting up a designated spot for photo ops and meet ups! They also played BTS music in the lobby ..."

Reviewed on Aug 30, 2026

Get rates
Hilton Chicago
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (3,440 reviews)
"I booked my stay 2 months in advance, but when I checked in, the nice lady assisting us had a hard time finding a room for us. She thanked us for our patience by giving us a voucher for 1 to get food from their store. We got to the room and found it dirty. There was a false eyelash from the previous ..."

Reviewed on Aug 30, 2026

Get rates
Hyatt Regency Chicago
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 ...
Get rates
River Hotel
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Get rates
The Allegro Royal Sonesta Hotel Chicago Loop
See all 5,383 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 ...
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! (1,715 reviews)
"All good like always"

Reviewed on Aug 30, 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 ...
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 ...
8.4/10 Very Good! (1,004 reviews)
"Front desk employees were so helpful and nice! Their staff clean the room daily so that was nice to come back to a clean room. Close to the Blue Line train mean easy access to public transportation. Will be back!"

Reviewed on Aug 30, 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 ...
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 ...
6/10 (1,004 reviews)
"I would probably avoid this place unless it's a last minute, overnight stay. There's a lot of sketchy things admit this place. From the moment I walked into reception it literally smelled like poop. If i were able to cancel the reservation then I would've."

Reviewed on Aug 28, 2026

Get rates
Carlton Inn Midway
See all 5,383 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.