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 $63

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

Frontier Airlines
Wed, Oct 14 - Wed, Oct 28
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 1 hour ago
$63
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 28, priced at $63 found 1 hour ago
Frontier Airlines
Thu, Oct 29 - Mon, Nov 16
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$85 Roundtrip, just found
$85
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Oct 29 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Nov 16, priced at $85 just found
Frontier Airlines
Wed, Oct 28 - Sun, Nov 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$95 Roundtrip, found 4 hours ago
$95
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Oct 28 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Nov 1, priced at $95 found 4 hours ago
Frontier Airlines
Thu, Oct 29 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$100 Roundtrip, found 9 hours ago
$100
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Thu, Oct 29 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Thu, Nov 19, priced at $100 found 9 hours ago
Frontier Airlines
Thu, Oct 29 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$110 Roundtrip, found 9 hours ago
$110
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Thu, Oct 29 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Thu, Nov 19, priced at $110 found 9 hours ago
Frontier Airlines
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $138 just found
Bargain Flight
Sat, Oct 24 - Tue, Nov 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$178 Roundtrip, found 2 hours ago
$178
Roundtrip
found 2 hours ago
Select Bargain Flight flight, departing Sat, Oct 24 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Nov 10, priced at $178 found 2 hours ago
American Airlines
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Select American Airlines flight, departing Sat, Oct 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $217 just found
Delta
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$227 Roundtrip, just found
$227
Roundtrip
just found
Select Delta flight, departing Sat, Oct 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $227 just found
Alaska Airlines
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, just found
$237
Roundtrip
just found
Select Alaska Airlines flight, departing Sat, Oct 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $237 just found
Southwest Airlines
Thu, Oct 29 - Mon, Nov 16
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$251 Roundtrip, just found
$251
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Oct 29 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Nov 16, priced at $251 just found
Southwest Airlines
Mon, Sep 28 - Tue, Oct 6
LAX
Los Angeles Intl.
MDW
Midway Intl.
$261 Roundtrip, found 1 hour ago
$261
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Mon, Sep 28 from Los Angeles Intl. to Midway Intl., returning Tue, Oct 6, priced at $261 found 1 hour ago
American Airlines
Fri, Sep 11 - Sun, Sep 13
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$379 Roundtrip, found 4 days ago
$379
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Sep 11 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sun, Sep 13, priced at $379 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Sep 21 - Sat, Sep 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$467 Roundtrip, found 9 hours ago
$467
Roundtrip
found 9 hours 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 $467 found 9 hours ago
Delta
Tue, Sep 15 - Tue, Sep 15
ECP
Northwest Florida Beaches Intl.
MDW
Midway Intl.
$479 Roundtrip, found 2 hours ago
$479
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Sep 15 from Northwest Florida Beaches Intl. to Midway Intl., returning Tue, Sep 15, priced at $479 found 2 hours ago
American Airlines
Tue, Sep 15 - Fri, Sep 18
ECP
Northwest Florida Beaches Intl.
ORD
O'Hare Intl.
$491 Roundtrip, found 9 hours ago
$491
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Sep 15 from Northwest Florida Beaches Intl. to O'Hare Intl., returning Fri, Sep 18, priced at $491 found 9 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 October, 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 $63, 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 $63 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$63

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! (10,307 reviews)
"Perfectly sufficient for the age of the property."

Reviewed on Sep 7, 2026

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! (2,179 reviews)
"They never refreshed our room. Disappointed because a great location."

Reviewed on Sep 7, 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! (889 reviews)
"Great location, the place has everything you need. Would stay again."

Reviewed on Sep 7, 2026

Get rates
Kasa Magnificent Mile 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 ...
8.8/10 Excellent! (5,423 reviews)
"The pictures shown when you book the room are not accurate to the room you will actually be given. Our room was very small with no fridge."

Reviewed on Sep 7, 2026

Get rates
River Hotel
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 ...
8/10 Very Good! (1,585 reviews)
"Stay was horrible. We didn’t have any AC the whole entire stay."

Reviewed on Sep 7, 2026

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! (3,170 reviews)
"Staff was amazing! Everyone was so helpful. Room was nice. Enough elevators that you aren't standing around."

Reviewed on Sep 7, 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! (3,519 reviews)
"Acceptable room and shower. Food was average. We used Valet Parking for 120 dollars/ day which seemed really steep altho the information at entrance said 65/d. Wd suggest really checking on this aspect."

Reviewed on Sep 7, 2026

Get rates
Hyatt Regency Chicago
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
9.6/10 Exceptional! (4,752 reviews)
"The hotel is clean and the staff is nice but there’s not a lot of amenities. If you don’t ask what it is included the staff won’t tell you."

Reviewed on Sep 7, 2026

Get rates
L7 Chicago by LOTTE
See all 5,387 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 ...
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! (2,392 reviews)
"Great place to stay. Wonderful staff and clean rooms. Breakfast with many options to accommodate varied preferences."

Reviewed on Sep 3, 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 ...
8.4/10 Very Good! (1,004 reviews)
"Bar staff had one waitress that was rude."

Reviewed on Sep 7, 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! (2,212 reviews)
"Bathroom and shower were immaculate."

Reviewed on Sep 7, 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 ...
6/10 (1,004 reviews)
"Not the worst place I've ever stayed, but a close second. Hard to think of anything that was not broken or inoperable."

Reviewed on Sep 7, 2026

Get rates
Carlton Inn Midway
See all 5,387 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.