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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 , 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 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 , 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 right now, why wait?
Destination airport | Midway Intl. |
|---|---|
Destination airport IATA code | MDW |
Roundtrip price | $400 |
Last Minute Hotel Deals in Chicago
Hilton Chicago/Magnificent Mile Suites
👍
Reviewed on Dec 15, 2025
Silversmith Hotel Chicago Downtown
Didn't eat breakfast at the hotel cause went to wildberry pancakes and Cafe but everything else was great
Reviewed on Dec 15, 2025
Club Quarters Hotel Wacker at Michigan, Chicago
Great friendy staff, Smooth Check-in Check-out Process and the view from the room was just stunning.
Reviewed on Dec 16, 2025
Palmer House a Hilton Hotel
Clean room. I didn’t mind the old door knobs I liked it. Smaller room than anticipated but it was nice and clean.
Reviewed on Dec 14, 2025
Hilton Chicago O'Hare Airport
right next to the airport. if you stay here here, exit from the front door, take a left and walk to the end of the hotel, and cross the street with a crossing guard, and you are at the airport sliding doors. quick to catch a flight staying here. also, the hotel has a great Jazz bar with live performances. ...
Reviewed on Dec 9, 2025
Embassy Suites by Hilton Chicago Downtown River North
Great place always.
Reviewed on Dec 12, 2025
Eurostars Magnificent Mile
It’s was very nice and cozy
Reviewed on Dec 15, 2025
Congress Plaza Hotel
The room was clean and the staff also good. The continental breakfast was not good.
Reviewed on Dec 15, 2025
Top Hotels With Free Airport Shuttle
Super 8 by Wyndham Chicago O'Hare Airport
Very nice hotel with a free airport shuttle. Highly recommend
Reviewed on Dec 14, 2025
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Good service
Reviewed on Dec 14, 2025
Hampton Inn Chicago-O'Hare International Airport
The room was clean and comfortable. Grace at the front desk was especially helpful. It was a bad flight, we were stuck in Chicago overnight with no toiletries, and Grace went out of her way to help us. Her kindness was much appreciated.
Reviewed on Dec 16, 2025
Holiday Inn Chicago O'Hare Area by IHG
I stay in the hotel every time I visit my kids. Staff is extremely friendly and helpful. Rooms are comfortable and clean. I will continue to stay there.
Reviewed on Dec 6, 2025
Loews Chicago O'Hare Hotel
Maggie was great and very accommodating. After what seemed like an eternity of failed attempts of getting home today. United ended up not loading our luggage! However, Maggie to the rescue with toothbrushes, deodorant and makeup remover!
Reviewed on Dec 15, 2025
Carlton Inn Midway
The room was clean and satisfied our needs. Was handy using their shuttle to Midway Airport.
Reviewed on Dec 7, 2025
Nearby Cities
Popular Flights to Chicago
- Los Angeles to Chicago
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- Phoenix to Chicago
- Rome to Chicago
- Houston to Chicago
- Las Vegas to Chicago
- Montreal to Chicago
- Moscow to Chicago
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- New Orleans to Chicago
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- Washington to Chicago
- Berlin to Chicago
- Hartford to Chicago
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