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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 | $141 |
Last Minute Hotel Deals in Chicago
Congress Plaza Hotel
"Great location and clean"
Reviewed on May 29, 2026
Hotel Riu Plaza Chicago
"Nice place"
Reviewed on May 29, 2026
The Chicago Hotel Collection - Magnificent Mile
"The hotel was amazing looked exactly like the photos. The staff was awesome 10/10 I would for sure stay here again!"
Reviewed on May 29, 2026
Hotel Felix River North/Magnificent Mile
"The hotel location and room was nice. I didn’t like that you had to pay $5 per bag for storage if you wanted to check out if the room early. I thought giving the room before noon would be better for them especially since I was coming back before that checkout time. So I just brought my stuff back ..."
Reviewed on May 29, 2026
Fairmont Chicago at Millennium Park
"I rented a suite. It was relatively very expensive so I expect more. There was orange seeds on the floor and a piece of orange peel and some M&M shell pieces on the floor when I arrived. The staff were just fair when I asked were certain things wise. It was almost like I expected me to know use terms ..."
Reviewed on May 28, 2026
Holiday Inn Chicago Dwtn - The Mart by IHG
"Good"
Reviewed on May 28, 2026
Freehand Chicago
"Not very clean at all. Comforters were stain even the ones we asked for after seeing the ones in the bed were stained. The curtains were stain, old and wore out with holes. Not convenient at all even for parking."
Reviewed on May 29, 2026
Crowne Plaza Chicago West Loop by IHG
"Staff were not easy to talk to and they were “busy”!"
Reviewed on May 29, 2026
Top Hotels With Free Airport Shuttle
Super 8 by Wyndham Chicago O'Hare Airport
"Olía mucho a cigarro y se escuchaba el ruido de las otras habitaciones"
Reviewed on May 29, 2026
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
"The front desk people were very unhelpful. I presented them with pictures & videos of rodents in the bed. They said I can reach out to Expedia for a full refund, when I reached out to Expedia they said the hotel only approved of a $24 refund. This is completely ridiculous. I didn’t pay to sleep with ..."
Reviewed on May 27, 2026
Hampton Inn Chicago-O'Hare International Airport
"Helpful"
Reviewed on May 29, 2026
Holiday Inn Chicago O'Hare Area by IHG
"Good place to stay when traveling out of O'Hare. Older property but well maintained. Great staff, clean and comfortable rooms. No extra charge for parking."
Reviewed on May 28, 2026
Loews Chicago O'Hare Hotel
"the fact that it was mentioned that the rooms are soundproof was not at all true. even after booking a 4 star hotel, my overallexperience was bad. I specifically booked a luxury hotel to give my family the best experience as it was their first time in chicago, but everyone of us could literally hear ..."
Reviewed on May 28, 2026
Carlton Inn Midway
"Towels were old and stain. Lights in the bathroom didn’t work we had to use the bathroom with the lights off. I brought it up to the front desk lady and all she said it was probably because of the rain and didn’t offer a different room or someone to come and fix. I asked for more towels and they ..."
Reviewed on May 29, 2026
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