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Chicago

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Chicago Flights as Low as $53

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

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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.

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 May, 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 $53, 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 $53 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
$50

Last Minute Hotel Deals in Chicago

Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
The price is $82 per night from Apr 29 to Apr 30
$82
per night
Apr 29 - Apr 30
Stay at this 4-star boutique hotel in Chicago. Enjoy a 24-hour health club, onsite parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
7.8/10 Good! (1,000 reviews)
"The front staff stated they had no access to laundry. I was needing an extra blanket and did not receive."

Reviewed on Apr 22, 2024

Hotel Felix River North/Magnificent Mile
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $143 per night from Apr 28 to Apr 29
$143
per night
Apr 28 - Apr 29
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (6,584 reviews)
"Good location"

Reviewed on Apr 21, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $139 per night from Apr 28 to Apr 29
$139
per night
Apr 28 - Apr 29
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! (2,800 reviews)
"The room wasn't done during my stay"

Reviewed on Apr 22, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
The price is $160 per night from Apr 28 to Apr 29
$160
per night
Apr 28 - Apr 29
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,858 reviews)
"The views from the room was amazing, quick access to fine dining and the staff was very friendly and welcoming."

Reviewed on Apr 21, 2024

Eurostars Magnificent Mile
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3 out of 5
243 E. Ontario, Chicago, IL
The price is $98 per night from Apr 28 to Apr 29
$98
per night
Apr 28 - Apr 29
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (2,179 reviews)
"Great hospitality"

Reviewed on Apr 22, 2024

Aloft Chicago Mag Mile
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 $129 per night from Apr 28 to Apr 29
$129
per night
Apr 28 - Apr 29
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! (3,001 reviews)
Short weekend trip!
"It was a nice stay. First time in this hotel. Would come back. Only issue was the toilet stopped up twice after barely using it where we had to request maintenance. Additionally, the air conditioner never got cold. We had it turned down to 65 degrees and it never got that low. Was about 10-15 degrees ..."

Reviewed on Apr 22, 2024

Club Quarters Hotel, Central Loop, 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 $194 per night from Apr 28 to Apr 29
$194
per night
Apr 28 - Apr 29
Stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
8.6/10 Excellent! (1,553 reviews)
"Excellent location, friendly staff, and outstanding pool."

Reviewed on Apr 22, 2024

InterContinental Chicago Magnificent Mile, an IHG Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is $167 per night from Apr 28 to Apr 29
$167
per night
Apr 28 - Apr 29
Stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,006 reviews)
"The hotel was very nice. However, I was not expecting the $25 resort fee per day. I found it difficult to use since I was staying at the hotel for a conference. Most meals were provided. We only went to the hotel restaurant one evening for dinner."

Reviewed on Apr 21, 2024

The Westin Michigan Avenue 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

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 25 to Apr 26
$75
per night
Apr 25 - Apr 26
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 (1,001 reviews)
"Great place to stay at, close to the airport and has shuttles to and from the airport!"

Reviewed on Apr 19, 2024

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
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 $80 per night from Apr 28 to Apr 29
$80
per night
Apr 28 - Apr 29
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! (1,002 reviews)
"Everything is good"

Reviewed on Apr 24, 2024

Super 8 by Wyndham Chicago O'Hare Airport
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 $109 per night from Apr 25 to Apr 26
$109
per night
Apr 25 - Apr 26
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! (1,281 reviews)
"Good"

Reviewed on Apr 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 $103 per night from Apr 28 to Apr 29
$103
per night
Apr 28 - Apr 29
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast. Our guests praise the breakfast and the helpful staff in our reviews. ...
7.4/10 Good! (1,003 reviews)
"Clean hotel. Staff was friendly."

Reviewed on Apr 9, 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 $165 per night from May 25 to May 26
$165
per night
May 25 - May 26
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! (1,508 reviews)
"Great experience"

Reviewed on Apr 23, 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 Apr 25 to Apr 26
$119
per night
Apr 25 - Apr 26
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 property was at a great location and close to shopping & events. Nice stay."

Reviewed on Apr 8, 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.