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Chicago

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Chicago Flights as Low as $51

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Spirit Airlines
Spirit Airlines
Frontier Airlines
Spirit Airlines
Frontier Airlines
Frontier Airlines
Alaska Airlines
United
Delta
American Airlines
Delta
Delta
Sun Country Airlines
JetBlue Airways
Delta

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.

Just the right flight

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.

Frequently Asked Questions About flights to Chicago

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 January, 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 16 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 $51, 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 $51 right now, why wait?

Can I fly to Chicago right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to  right now?” When it’s time to book your flight, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$51

Last Minute Hotel Deals in Chicago

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
The price is $89 per night from Dec 14 to Dec 15
$89
per night
Dec 14 - Dec 15
Stay at this 4-star family-friendly hotel in Chicago. Enjoy WiFi, a 24-hour fitness center, and valet parking. Our guests praise the helpful staff and the clean ...
7.4/10 Good! (2,100 reviews)
"Room was clean, well decorated and comfortable. I was pleasantly surprised by how lovely the room was. I highly recommend and will stay again!"

Reviewed on Nov 26, 2023

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $116 per night from Dec 3 to Dec 4
$116
per night
Dec 3 - Dec 4
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.4/10 Good! (5,922 reviews)
"Great view on park, good location."

Reviewed on Nov 28, 2023

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $89 per night from Jan 1 to Jan 2
$89
per night
Jan 1 - Jan 2
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,228 reviews)
"Best location in Chicago"

Reviewed on Nov 30, 2023

River Hotel
Hyatt Regency Chicago
Hyatt Regency Chicago