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Chicago Flights as Low as $87
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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 $87, 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 $87 right now, why wait?
Destination airport | O'Hare Intl. |
Destination airport IATA code | ORD |
Roundtrip price | $63 |
Last Minute Hotel Deals in Chicago

The Wade
Reviewed on Aug 20, 2025

Congress Plaza Hotel
Reviewed on Aug 21, 2025

Embassy Suites by Hilton Chicago Downtown River North
Reviewed on Aug 22, 2025

Palmer House a Hilton Hotel
Reviewed on Aug 21, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Reviewed on Aug 21, 2025

Freehand Chicago
Reviewed on Aug 21, 2025

Hilton Chicago/Magnificent Mile Suites
Reviewed on Aug 20, 2025

citizenM Chicago Downtown
Reviewed on Aug 21, 2025
Top Hotels With Free Airport Shuttle

Super 8 by Wyndham Chicago O'Hare Airport
Reviewed on Aug 14, 2025

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Reviewed on Aug 19, 2025

Hampton Inn Chicago-O'Hare International Airport
Reviewed on Aug 19, 2025

Holiday Inn Chicago O'Hare Area by IHG
Reviewed on Aug 16, 2025

Loews Chicago O'Hare Hotel
Reviewed on Aug 20, 2025

Carlton Inn Midway
Reviewed on Aug 17, 2025
Nearby Cities
Popular Flights to Chicago
- Los Angeles to Chicago
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Popular Flight Routes
- Atlanta to New York
- Detroit to Las Vegas
- Dallas to Atlanta
- Dallas to Yosemite National Park
- Toronto to Edmonton
- Chicago to Tulum
- Houston to Lake Tahoe
- Chicago to Las Vegas
- Dallas to Miami
- Dallas to Lake Tahoe
- New York to Miami
- New York to Las Vegas
- Miami to Atlanta
- Minneapolis St Paul to Fort Walton Beach Destin
- Dallas to Branson
- Cleveland to Vero Beach
- Managua to Miami
- Atlanta to Boston
- Austin to Tulum
- Calgary to Vancouver