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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
Tue, Jun 11 - Tue, Jun 11
BOS
Logan Intl.
ORD
O'Hare Intl.
$51 Roundtrip, found 3 days ago
$51
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Jun 11 from Logan Intl. to O'Hare Intl., returning Tue, Jun 11, priced at $51 found 3 days ago
Frontier Airlines
Wed, Aug 28 - Wed, Sep 4
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 28 from Charlotte-Douglas Intl. to O'Hare Intl., returning Wed, Sep 4, priced at $58 found 1 day ago
Spirit Airlines
Tue, Jun 11 - Thu, Jun 13
BOS
Logan Intl.
ORD
O'Hare Intl.
$62 Roundtrip, found 3 days ago
$62
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Jun 11 from Logan Intl. to O'Hare Intl., returning Thu, Jun 13, priced at $62 found 3 days ago
Spirit Airlines
Sun, Sep 15 - Tue, Sep 17
BOS
Logan Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 16 hours ago
$63
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Sun, Sep 15 from Logan Intl. to O'Hare Intl., returning Tue, Sep 17, priced at $63 found 16 hours ago
Spirit Airlines
Tue, Aug 27 - Wed, Sep 4
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$65 Roundtrip, found 1 day ago
$65
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Aug 27 from Charlotte-Douglas Intl. to O'Hare Intl., returning Wed, Sep 4, priced at $65 found 1 day ago
Frontier Airlines
Mon, Aug 26 - Wed, Sep 4
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$67 Roundtrip, found 1 day ago
$67
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Aug 26 from Charlotte-Douglas Intl. to O'Hare Intl., returning Wed, Sep 4, priced at $67 found 1 day ago
Spirit Airlines
Tue, Jun 11 - Wed, Jun 12
BOS
Logan Intl.
ORD
O'Hare Intl.
$69 Roundtrip, found 3 days ago
$69
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Jun 11 from Logan Intl. to O'Hare Intl., returning Wed, Jun 12, priced at $69 found 3 days ago
Spirit Airlines
Tue, Jul 16 - Wed, Jul 17
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$71 Roundtrip, found 2 days ago
$71
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Jul 16 from George Bush Intercontinental to O'Hare Intl., returning Wed, Jul 17, priced at $71 found 2 days ago
Spirit Airlines
Thu, Sep 12 - Thu, Sep 12
BOS
Logan Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 1 day ago
$73
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Sep 12 from Logan Intl. to O'Hare Intl., returning Thu, Sep 12, priced at $73 found 1 day ago
Frontier Airlines
Thu, Sep 5 - Tue, Sep 10
IAH
George Bush Intercontinental
MDW
Midway Intl.
$77 Roundtrip, found 2 days ago
$77
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Sep 5 from George Bush Intercontinental to Midway Intl., returning Tue, Sep 10, priced at $77 found 2 days ago
United
Wed, Jul 24 - Sat, Jul 27
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select United flight, departing Wed, Jul 24 from George Bush Intercontinental to O'Hare Intl., returning Sat, Jul 27, priced at $137 found 1 day ago
American Airlines
Tue, Jul 16 - Wed, Jul 17
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jul 16 from George Bush Intercontinental to O'Hare Intl., returning Wed, Jul 17, priced at $137 found 2 days ago
Frontier Airlines
Thu, Jun 6 - Sat, Jun 8
CLT
Charlotte-Douglas Intl.
MDW
Midway Intl.
$142 Roundtrip, found 4 days ago
$142
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Jun 6 from Charlotte-Douglas Intl. to Midway Intl., returning Sat, Jun 8, priced at $142 found 4 days ago
Delta
Sun, Sep 1 - Sun, Sep 1
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Sep 1 from Charlotte-Douglas Intl. to O'Hare Intl., returning Sun, Sep 1, priced at $169 found 1 day ago
JetBlue Airways
Wed, Jun 5 - Wed, Jun 5
BOS
Logan Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 2 days ago
$172
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Jun 5 from Logan Intl. to O'Hare Intl., returning Wed, Jun 5, priced at $172 found 2 days ago
Sun Country Airlines
Wed, Jul 3 - Sun, Jul 7
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$332 Roundtrip, found 9 hours ago
$332
Roundtrip
found 9 hours ago
Select Sun Country Airlines flight, departing Wed, Jul 3 from Charlotte-Douglas Intl. to O'Hare Intl., returning Sun, Jul 7, priced at $332 found 9 hours ago

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 June, 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
$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 $140 per night from Jul 1 to Jul 2
$140
per night
Jul 1 - Jul 2
Stay at this 4-star boutique hotel in Chicago. Enjoy a 24-hour health club, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff ...
7.8/10 Good! (1,014 reviews)
"Beautiful hotel, very central, walking distance of so many amenities. Safe and clean. Will book again for another stay"

Reviewed on May 30, 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 $188 per night from Jun 16 to Jun 17
$188
per night
Jun 16 - Jun 17
Book a 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 ...
7.6/10 Good! (6,819 reviews)
"It was an okay stay because they switched our room from a room that had a door in the middle between 2 different rooms that wouldn’t lock and had a key hole where someone can look through and move the knob while your sleeping and switched us to a 3 bed room that felt much safer!! Cleanliness was ..."

Reviewed on May 31, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $166 per night from Jul 1 to Jul 2
$166
per night
Jul 1 - Jul 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! (2,912 reviews)
"The facility was beautiful. The staff was extremely friendly and helpful. The views of the city were phenomenal."

Reviewed on May 28, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
The price is $170 per night from Jun 30 to Jul 1
$170
per night
Jun 30 - Jul 1
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 ...
8.4/10 Very Good! (1,995 reviews)
"We stayed for a weekend get a way and it was perfect."

Reviewed on May 31, 2024

Eurostars Magnificent Mile
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 $222 per night from Jun 30 to Jul 1
$222
per night
Jun 30 - Jul 1
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
8/10 Very Good! (2,328 reviews)
Great hotel for family
"The hotel and room were spacious and clean. The breakfast was terrific. We had a couple problems with our room during our stay but management took care of the problems quickly, even when one took place at 3 am. The location was close to public transportation and many restaurants."

Reviewed on May 30, 2024

Embassy Suites by Hilton Chicago Downtown River North
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 $234 per night from Jul 2 to Jul 3
$234
per night
Jul 2 - Jul 3
Book a stay at this historic hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the pool in our ...
8.6/10 Excellent! (1,632 reviews)
"LOCATION LOCATION LOCATION EASY ACCESS TO EVERYTHING in Chicago, plus it has the Michael Jordan Steak House which is a must while staying there."

Reviewed on May 31, 2024

InterContinental Chicago Magnificent Mile, an IHG Hotel
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 $149 per night from Jul 1 to Jul 2
$149
per night
Jul 1 - Jul 2
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
8.4/10 Very Good! (3,062 reviews)
"Great"

Reviewed on May 29, 2024

Club Quarters Hotel, Central Loop, Chicago
Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
4 out of 5
O'Hare International Airport, Chicago, IL
The price is $191 per night from Jun 21 to Jun 22
$191
per night
Jun 21 - Jun 22
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the clean rooms ...
7.6/10 Good! (1,968 reviews)
"Always a pleasure to stay at this Hilton when our travel is delayed and we have missed our connecting flight!"

Reviewed on May 28, 2024

Hilton Chicago O'Hare Airport
See all 4,939 properties in 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 $86 per night from Jun 3 to Jun 4
$86
per night
Jun 3 - Jun 4
Book a 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 ...
7.8/10 Good! (1,004 reviews)
"The hotel was awesome. Clean and very quiet. We loved the shuttle service to the airport. Why park in Chicago for $40 a day when you can stay there and ride the train for $5 all day long."

Reviewed on May 27, 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 $93 per night from Jun 9 to Jun 10
$93
per night
Jun 9 - Jun 10
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)
"Still can tell its and old facility, but the front desk was helpful"

Reviewed on May 28, 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 $119 per night from Jun 16 to Jun 17
$119
per night
Jun 16 - Jun 17
Book a 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 ...
9/10 Wonderful! (1,306 reviews)
"We always know what to expect with a Hampton. This is a very nice one. The beds are amazing and the decor is fresh. Having a shuttle from the airport is priceless. Great pick!"

Reviewed on May 30, 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 $112 per night from Jun 16 to Jun 17
$112
per night
Jun 16 - Jun 17
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
7.4/10 Good! (1,002 reviews)
"Quick checkin, complementary airport shuttle service"

Reviewed on May 29, 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 $189 per night from Jun 30 to Jul 1
$189
per night
Jun 30 - Jul 1
Stay at this 4.5-star luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the ...
9.2/10 Wonderful! (1,557 reviews)
"Very clean. Close to.ohare. nice quick shuttle ride ro airport. Restaurant had good food."

Reviewed on May 29, 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 Jun 2 to Jun 3
$119
per night
Jun 2 - Jun 3
Book a 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 ...
7/10 Good! (1,002 reviews)
"Was noisy. But I did like the convenance of the shuttle to the airport. And the staff were all very pleasant."

Reviewed on May 20, 2024

Carlton Inn Midway
See all 4,939 properties in 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.