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Chicago

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Chicago Flights as Low as $41

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

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United
Delta
American Airlines
Delta
JetBlue Airways
Alaska Airlines

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 April, 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 $41, 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 $41 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
$40

Last Minute Hotel Deals in Chicago

Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
The price is $94 per night from Mar 24 to Mar 25
$94
per night
Mar 24 - Mar 25
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and room service. Our guests praise the restaurant and the helpful staff ...
8.4/10 Very Good! (2,874 reviews)
"My whole experience with this hotel was fantastic. All of the staff were friendly and accommodating. Lovely rooms , quiet and great ammenities. Loved the Nespresso machine and hand/body lotion . Danny at check out was one of the friendliest people I’ve meet at any hotel I’ve stayed at . Was interested ..."

Reviewed on Mar 17, 2024

Club Quarters Hotel, Central Loop, Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $125 per night from Apr 1 to Apr 2
$125
per night
Apr 1 - Apr 2
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 ...
7.6/10 Good! (6,337 reviews)
"Nice location. Historic building with charm, but not shiny and new. Bed was extremely comfortable but my room faced the L so it was rather noisy. Maintenance being done on elevators on a busy friday night was inconvenient."

Reviewed on Mar 16, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $109 per night from Mar 31 to Apr 1
$109
per night
Mar 31 - Apr 1
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! (2,658 reviews)
Great Stay
"Fantastic location, great service and a wonderful room."

Reviewed on Mar 18, 2024

River Hotel
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
3.5 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
The price is $125 per night from Mar 31 to Apr 1
$125
per night
Mar 31 - Apr 1
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the pool and the helpful staff in ...
8.6/10 Excellent! (1,004 reviews)
"To complicated"

Reviewed on Mar 14, 2024

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
W Chicago - Lakeshore
W Chicago - Lakeshore
4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
The price is $149 per night from Mar 28 to Mar 29
$149
per night
Mar 28 - Mar 29
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast, WiFi, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,005 reviews)
"A1"

Reviewed on Mar 17, 2024

W Chicago - Lakeshore
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is $132 per night from Mar 22 to Mar 23
$132
per night
Mar 22 - Mar 23
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,002 reviews)
"Fabulous hotel! Will stay here whenever I travel to Chicago!"

Reviewed on Mar 10, 2024

The Westin Michigan Avenue Chicago
InterContinental Chicago Magnificent Mile, an IHG Hotel
InterContinental Chicago Magnificent Mile, an IHG Hotel
4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is $170 per night from Mar 31 to Apr 1
$170
per night
Mar 31 - Apr 1
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (1,488 reviews)
"Large room, easy check in, clean environment."

Reviewed on Mar 17, 2024

InterContinental Chicago Magnificent Mile, an IHG Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
The price is $94 per night from Mar 20 to Mar 21
$94
per night
Mar 20 - Mar 21
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 ...
7.6/10 Good! (2,406 reviews)
"Older well renovated property. Minor drains problems with potty with room."

Reviewed on Mar 16, 2024

Warwick Allerton - Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Hotels With Free Airport Shuttle

Super 8 by Wyndham Chicago O'Hare Airport
Super 8 by Wyndham Chicago O'Hare Airport
2.5 out of 5
2951 Touhy Ave, Elk Grove Village, IL
The price is $72 per night from Mar 20 to Mar 21
$72
per night
Mar 20 - Mar 21
Stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (1,003 reviews)
Clean, on the highway, large room
"Just got here😃"

Reviewed on Mar 16, 2024

Super 8 by Wyndham Chicago O'Hare Airport
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
3 out of 5
777 East Grand Avenue, Bensenville, IL
The price is $75 per night from Apr 3 to Apr 4
$75
per night
Apr 3 - Apr 4
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.4/10 (1,002 reviews)
"."

Reviewed on Mar 11, 2024

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Hampton Inn Chicago-O'Hare International Airport
Hampton Inn Chicago-O'Hare International Airport
2.5 out of 5
3939 N Mannheim Rd, Schiller Park, IL
The price is $89 per night from Mar 24 to Mar 25
$89
per night
Mar 24 - Mar 25
Stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,249 reviews)
"I would go back."

Reviewed on Mar 17, 2024

Hampton Inn Chicago-O'Hare International Airport
Holiday Inn Chicago O'Hare Area, an IHG Hotel
Holiday Inn Chicago O'Hare Area, an IHG Hotel
3 out of 5
5615 North Cumberland Avenue, Chicago, IL
The price is $94 per night from Mar 31 to Apr 1
$94
per night
Mar 31 - Apr 1
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast. Our guests praise the breakfast and the helpful staff in ...
7.4/10 Good! (1,000 reviews)
"Does everything it’s supposed to do."

Reviewed on Mar 10, 2024

Holiday Inn Chicago O'Hare Area, an IHG Hotel
Loews Chicago O'Hare Hotel
Loews Chicago O'Hare Hotel
4.5 out of 5
5300 N River Rd, Rosemont, IL
The price is $169 per night from Mar 20 to Mar 21
$169
per night
Mar 20 - Mar 21
Stay at this 4.5-star luxury hotel in Rosemont. Enjoy free WiFi, breakfast, and a free airport shuttle. Our guests praise the restaurant and the helpful staff ...
9.2/10 Wonderful! (1,482 reviews)
"The hotel used to be better than this. But, still a decent business hotel."

Reviewed on Mar 18, 2024

Loews Chicago O'Hare Hotel
Carlton Inn Midway
Carlton Inn Midway
2 out of 5
4944 S Archer Ave, Chicago, IL
The price is $119 per night from Mar 20 to Mar 21
$119
per night
Mar 20 - Mar 21
Stay at this business-friendly motel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.2/10 Good! (1,003 reviews)
"The staff members were super nice, I felt a little unsafe on my first day but eventually got used to it for the rest of the weekend. Really comfy rooms too."

Reviewed on Mar 11, 2024

Carlton Inn Midway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.