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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 | $406 |
Last Minute Hotel Deals in Chicago
Embassy Suites by Hilton Chicago Downtown River North
It was fine
Reviewed on Nov 5, 2025
Congress Plaza Hotel
Yes
Reviewed on Nov 3, 2025
Hilton Chicago/Magnificent Mile Suites
Great staff at the front desk!
Reviewed on Nov 2, 2025
citizenM Chicago Downtown
Everything was fantastic!
Reviewed on Nov 3, 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Clean rooms and friendly staff
Reviewed on Nov 3, 2025
Aloft Chicago Mag Mile
Male staff members were nice and helpful. The full bar was great. The interior was stylish, and I loved the fireplace with its cozy atmosphere. I stayed here for 1 week.
Reviewed on Nov 3, 2025
Freehand Chicago
Staff interactions were excellent in every aspect.
Reviewed on Nov 2, 2025
The Whitehall Hotel, BW Premier Collection
Best upon arrival and the staff promptly answered any and all concerns
Reviewed on Nov 2, 2025
Top Hotels With Free Airport Shuttle
Super 8 by Wyndham Chicago O'Hare Airport
Location isn’t bad you will be close to airport
Reviewed on Nov 2, 2025
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Yes fresh but i stayed there for six days and it was the same everyday. It got boring real quick.
Reviewed on Nov 1, 2025
Hampton Inn Chicago-O'Hare International Airport
It was a nice room. The facilities were very clean. Breakfast was a bit busy and hard to find a seat.
Reviewed on Nov 4, 2025
Holiday Inn Chicago O'Hare Area by IHG
Professional staff, nice rooms, convenient location
Reviewed on Nov 4, 2025
Loews Chicago O'Hare Hotel
Gorgeous property maintained to the highest standards. Everything was perfecto!
Reviewed on Nov 3, 2025
Carlton Inn Midway
Very friendly! With airport shuttle!
Reviewed on Oct 18, 2025
Nearby Cities
Popular Flights to Chicago
- Los Angeles to Chicago
- London to Chicago
- New York to Chicago
- Orlando to Chicago
- Toronto to Chicago
- Dallas to Chicago
- Phoenix to Chicago
- Rome to Chicago
- Houston to Chicago
- Las Vegas to Chicago
- Montreal to Chicago
- Moscow to Chicago
- Paris to Chicago
- Detroit to Chicago
- Kansas City to Chicago
- New Orleans to Chicago
- San Francisco to Chicago
- 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