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Chicago

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Chicago Flights as Low as $48

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.

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 August, 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 $48, 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 $48 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$58

Last Minute Hotel Deals in Chicago

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $179 per night from Aug 25 to Aug 26
$179
includes taxes & fees
Aug 25 - Aug 26
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the comfy rooms and the overall ...
7.6/10 Good! (7,419 reviews)
"This is a great place to stay. This was my fourth time this summer so far. Each visit has been wonderful. Many people write this hotel off as "old". Wonderful. Spend hundreds more at a "new" hotel and enjoy their shoddy or unpredictable service. Thats what I've experienced, especially at Hilton ..."

Reviewed on Jul 24, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $175 per night from Aug 26 to Aug 27
$175
includes taxes & fees
Aug 26 - Aug 27
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the comfy rooms and the overall ...
8.6/10 Excellent! (3,142 reviews)
"Great experience."

Reviewed on Jul 25, 2024

River Hotel
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4 out of 5
17 E Monroe St, Chicago, IL
The price is $243 per night from Aug 23 to Aug 24
$243
includes taxes & fees
Aug 23 - Aug 24
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the comfy rooms and the ...
8/10 Very Good! (1,365 reviews)
"Good experience overall."

Reviewed on Jul 24, 2024

Palmer House a Hilton Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
The price is $200 per night from Aug 26 to Aug 27
$200
includes taxes & fees
Aug 26 - Aug 27
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the comfy rooms and the overall value ...
8.4/10 Very Good! (2,245 reviews)
"Pros: Great location and friendly staff. Comfortable beds. Cold water for guests in lobby. Cons: Odd use of curtain to create privacy between bathroom and bedroom (glass wall in shower). Blackout curtains to outside did not overlap and still let light through."

Reviewed on Jul 24, 2024

Eurostars Magnificent 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 $188 per night from Aug 25 to Aug 26
$188
includes taxes & fees
Aug 25 - Aug 26
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the comfy rooms and the overall ...
8.4/10 Very Good! (3,180 reviews)
"I liked the central Chicago downtown location of this hotel. A very walkable location, proximity to tourist attractions, easy access to the L and other transportation options."

Reviewed on Jul 23, 2024

Club Quarters Hotel, Central Loop, Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3 out of 5
10 E Grand Ave, Chicago, IL
The price is $184 per night from Aug 25 to Aug 26
$184
includes taxes & fees
Aug 25 - Aug 26
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
8/10 Very Good! (2,037 reviews)
"Great location, walkable to many sites, easy access to metro and many dining options in the area."

Reviewed on Jul 23, 2024

Hilton Garden Inn Chicago Downtown/Magnificent Mile
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 $206 per night from Aug 11 to Aug 12
$206
includes taxes & fees
Aug 11 - Aug 12
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the property condition in ...
8.6/10 Excellent! (1,010 reviews)
"Excellent location, hotel in good condition, several options for dinner."

Reviewed on Jul 24, 2024

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
The price is $258 per night from Aug 25 to Aug 26
$258
includes taxes & fees
Aug 25 - Aug 26
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the comfy rooms in our reviews. Popular attractions ...
8/10 Very Good! (2,660 reviews)
"Excellent staff!!!"

Reviewed on Jul 26, 2024

Embassy Suites by Hilton Chicago Downtown River North
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 $103 per night from Aug 25 to Aug 26
$103
includes taxes & fees
Aug 25 - Aug 26
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the overall value in our ...
7.6/10 Good! (1,003 reviews)
"close to the airport, shuttle for free and the shuttle came pretty fast, not expensive. The breakfast was as cheap as it can be but there is a Dunkin Donuts a 6 minute walk down the road (crossing the road is exciting) also though on the same side is a Subway Shop. The Staff was very friendly and ..."

Reviewed on Jul 24, 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 $113 per night from Aug 25 to Aug 26
$113
includes taxes & fees
Aug 25 - Aug 26
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Fashion Outlets of Chicago and Rosemont ...
6.4/10 (1,007 reviews)
"Nice clean space to stay"

Reviewed on Jul 23, 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 $141 per night from Jul 29 to Jul 30
$141
includes taxes & fees
Jul 29 - Jul 30
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the comfy rooms and the overall ...
9/10 Wonderful! (1,370 reviews)
"We checked into the hotel the evening on July 15, the same night a storm rolled in. It knocked out electricity at the hotel for about a full day a few more hours I think. I believe generators kicked in right away because we never went completely dark. Not having full electricity and having to use ..."

Reviewed on Jul 25, 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 $121 per night from Aug 25 to Aug 26
$121
includes taxes & fees
Aug 25 - Aug 26
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Rosemont Theatre and Fashion ...
7.4/10 Good! (1,006 reviews)
"The property was fine and very close to the L train station to downtown and to O'Hare. Breakfast was very good and the staff was very attentive in the restaurant. Room was spacious and clean. I would stay again."

Reviewed on Jul 25, 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 $204 per night from Jul 28 to Jul 29
$204
includes taxes & fees
Jul 28 - Jul 29
Stay at this 4.5-star luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the comfy rooms and the ...
9.2/10 Wonderful! (1,629 reviews)
"the people were very nice."

Reviewed on Jul 25, 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 $140 per night from Jul 28 to Jul 29
$140
includes taxes & fees
Jul 28 - Jul 29
Book a stay at this business-friendly motel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Popular attractions United Center and Guaranteed Rate ...
6.8/10 (1,005 reviews)
"Good value! Close to Midway and trains to downtown."

Reviewed on Jul 13, 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.