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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 | O'Hare Intl. |
|---|---|
Destination airport IATA code | ORD |
Roundtrip price | $115 |
Last Minute Hotel Deals in Chicago
Congress Plaza Hotel
"No heat, toilet was broken, no hot water. I left. Front staff was very rude. The staff who came to fix the toilet and bring me more blankets and a portable heater were very nice."
Reviewed on May 31, 2026
The Chicago Hotel Collection - Magnificent Mile
"Everything was great"
Reviewed on May 31, 2026
Hotel Riu Plaza Chicago
"This hotel is absolutely lovely! Immaculate in every area, with very helpful and friendly staff. The room was perfectly appointed. The bathroom door doubled as a door to the toilet and I want one of those in my house! The rain shower with a wand had great water pressure and temperature. I'm not a ..."
Reviewed on May 31, 2026
Hyatt Regency O'Hare Chicago
"Convenient to O’Hare with reliable shuttle that runs frequently. The hotel itself and staff exceeded expectations. Would definitely stay here again."
Reviewed on May 31, 2026
The Chicago Hotel Collection Ambassador Gold Coast
"No está especificado en expedía un cargo extra de $189 para poderte hospedar. Es obligatorio según el hotel."
Reviewed on May 31, 2026
Freehand Chicago
"Great price, the bunk beds were fun!"
Reviewed on Jun 1, 2026
Crowne Plaza Chicago West Loop by IHG
"It's near the union Station and convenient area, bus stop is near by"
Reviewed on May 31, 2026
Hotel Felix River North/Magnificent Mile
Top Hotels With Free Airport Shuttle
Super 8 by Wyndham Chicago O'Hare Airport
"A good breakfast selection friendly, staff convenience"
Reviewed on May 30, 2026
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
"Overall good experience and stuff very nice and helpful."
Reviewed on May 31, 2026
Hampton Inn Chicago-O'Hare International Airport
"Very convenient for access to O'hare."
Reviewed on May 31, 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
"Service was impeccable. All staff was kind and helpful. The rooms were a little plain but functional. Rooms were clean. The restaurant served good waffles and fruit."
Reviewed on May 31, 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
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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