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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 | $264 |
Last Minute Hotel Deals in Chicago
Palmer House a Hilton Hotel
Great
Reviewed on Jan 3, 2026
Hilton Chicago
The hotel property was amazing! Numerous options for dining and relaxing. The room was clean and inviting.
Reviewed on Jan 8, 2026
Hilton Chicago/Magnificent Mile Suites
Location
Reviewed on Jan 6, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
The staff was GREAT, room was clean but small.
Reviewed on Jan 3, 2026
Hilton Chicago O'Hare Airport
Our check in between flights was so friendly , efficient and competent . Ella is great . This easiest to access the property form terminal 2 .
Reviewed on Jan 5, 2026
Embassy Suites by Hilton Chicago Downtown River North
Clean room, good service
Reviewed on Jan 5, 2026
Eurostars Magnificent Mile
The view stood out the most to me and the room was very clean and stayed clean. Me and my partner really enjoyed our stay!
Reviewed on Jan 7, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Great food excellent service! Wonderful view!!!!
Reviewed on Jan 8, 2026
Top Hotels With Free Airport Shuttle
Super 8 by Wyndham Chicago O'Hare Airport
The room is clean. Breakfast is cool.
Reviewed on Jan 6, 2026
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Check-In was nice and smooth and they were very courteous and explained everything we needed to know while staying here
Reviewed on Jan 8, 2026
Hampton Inn Chicago-O'Hare International Airport
Friendly staff
Reviewed on Jan 3, 2026
Holiday Inn Chicago O'Hare Area by IHG
Great staff, great price and convenient location.
Reviewed on Dec 31, 2025
Loews Chicago O'Hare Hotel
Everything was great
Reviewed on Jan 7, 2026
Carlton Inn Midway
It is a good place to stay.
Reviewed on Jan 1, 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