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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
"Staff was super nice and attentive."
Reviewed on May 29, 2026
The Chicago Hotel Collection - Magnificent Mile
"rooftop"
Reviewed on May 29, 2026
Hotel Felix River North/Magnificent Mile
Fairmont Chicago at Millennium Park
"We really enjoyed our stay at this beautiful hotel! The hotel was extremely clean and the rooms were large and well designed. The amenities were top notch. The front desk staff were extremely knowledgeable and helpful. You can walk to any of the top attractions from this hotel and we put on 9 miles ..."
Reviewed on May 29, 2026
Holiday Inn Chicago Dwtn - The Mart by IHG
"A nice quiet hotel in downtown Chicago close to everything. Very comfortable room, and parking available too!"
Reviewed on May 29, 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
"Hotel parking was full. We were given other hotel parking locations in which we needed to use. We woke up the next morning, car window was shattered and our belongings stolen. Hotel could careless it happened."
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 only thing we noticed when we arrived for check in was, from the pool to the elevator, there was water all over the floor from ppl coming out of the pool. Someone could've slipped. And, the room we got, the bed was hard as a rock to sleep on. Other than that, the staff at the front desk was helpful ..."
Reviewed on May 30, 2026
Hampton Inn Chicago-O'Hare International Airport
"Everything was good and well done. We will plan to stay here again if we need to go to Chicago again."
Reviewed on May 29, 2026
Holiday Inn Chicago O'Hare Area by IHG
"Staff were very friendly and helpful, property and rooms very clean. Great shower, good hot and cold water. Small issue with keycard not working when we got back to the room, but staff corrected quickly. Perfect location. WiFi was not working well however."
Reviewed on May 30, 2026
Loews Chicago O'Hare Hotel
"Convenient location, but for the price the room was not very clean (bad body odor smell) and $40/day parking makes this a tough sell."
Reviewed on May 29, 2026
Carlton Inn Midway
"Staff are nice and helpful , Was missing some amenities “hand washing soap dispenser was empty i ask for a refill and never got it” Parking spacious and available Our Room had couple pf lights that’s not working asking for repairs and never got it The breakfast is variable and nice “some items ends ..."
Reviewed on May 29, 2026
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
- 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