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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 | $277 |
Last Minute Hotel Deals in Chicago
Hilton Chicago/Magnificent Mile Suites
Great front desk service
Reviewed on Dec 25, 2025
Palmer House a Hilton Hotel
Decent room and the staff at the front desk and restaurant were friendly and helpful. The front desk area is cramped and confusing (i.e.) once you get your key card from check-in, it is so tight in that area that that it’s unclear how you get out of the area without pushing past the people in line ...
Reviewed on Dec 22, 2025
Hilton Chicago
Very friendly staff.
Reviewed on Dec 26, 2025
Club Quarters Hotel Wacker at Michigan, Chicago
The hotel was great! Clean and spacious and I would stay there again. (Not in the same room but i would stay in the same hotel.) However, we were placed on the 40th floor in the only room on that floor with the elevator directly behind the bed. Every time the elevator moved, we heard loud mechanical ...
Reviewed on Dec 22, 2025
Hilton Chicago O'Hare Airport
Early check in available for $25, worth it for getting rest between flights. Very friendly staff
Reviewed on Dec 27, 2025
Silversmith Hotel Chicago Downtown
Friendly staff. Bar service slow but friendly unless you ask for a special order. They’ll get it for you but body language makes it clear it was not desired. Cleaning staff verybfirendsly and helpful.
Reviewed on Dec 27, 2025
Warwick Allerton - Chicago
clean room
Reviewed on Dec 26, 2025
Embassy Suites by Hilton Chicago Downtown River North
This is a great family friendly hotel. The breakfast in the morning was phenomenal. Threw my daughter at 13 th birthday celebration with one of her friends and they had a great time. Mom and Dad also had a great time as well. The only thing about this hotel is the parking. It was $80 a night so you ...
Reviewed on Dec 23, 2025
Top Hotels With Free Airport Shuttle
Super 8 by Wyndham Chicago O'Hare Airport
There was no trash in the lot or along the street. The lobby smelled so good. And people were sitting in the area where light breakfast is served. Very inviting. More importantly Chris was amazing familiar with my job as an aviation officer. Offer to let me sleep in extra hour before I did another ...
Reviewed on Dec 27, 2025
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Great place
Reviewed on Dec 25, 2025
Hampton Inn Chicago-O'Hare International Airport
Thank you for the front desk! They're very friendly and helpful
Reviewed on Dec 22, 2025
Holiday Inn Chicago O'Hare Area by IHG
The front desk staff was terrific; very friendly and knowledgeable about the surrounding area. The room was large and clean, as was the bathroom. This is an older property, but well-maintained and comfortable. It is located close to O'Hare and has a nice shuttle service. I will stay here again when ...
Reviewed on Dec 20, 2025
Loews Chicago O'Hare Hotel
Clean and quiet room
Reviewed on Dec 27, 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
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- Montreal to Chicago
- Moscow to Chicago
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- Berlin to Chicago
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Popular Flight Routes
- Atlanta to New York
- Detroit to Las Vegas
- Dallas to Atlanta
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- 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