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Chicago

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Chicago Flights as Low as $87

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

Frontier Airlines
Thu, Sep 11 - Thu, Sep 18
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$87 Roundtrip, found 2 days ago
$87
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Sep 11 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Thu, Sep 18, priced at $87 found 2 days ago
Frontier Airlines
Sat, Oct 11 - Sat, Oct 18
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$88 Roundtrip, found 2 days ago
$88
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Oct 11 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Sat, Oct 18, priced at $88 found 2 days ago
Spirit Airlines
Thu, Sep 18 - Thu, Sep 25
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$90 Roundtrip, found 2 days ago
$90
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Sep 18 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, Sep 25, priced at $90 found 2 days ago
Frontier Airlines
Tue, Oct 21 - Sat, Nov 1
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Oct 21 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Nov 1, priced at $98 found 2 days ago
Spirit Airlines
Sat, Sep 20 - Sat, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 2 days ago
$120
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Sep 20 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 20, priced at $120 found 2 days ago
American Airlines
Tue, Sep 30 - Tue, Sep 30
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 30 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Tue, Sep 30, priced at $134 found 1 day ago
United
Tue, Sep 30 - Wed, Oct 1
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 30 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Wed, Oct 1, priced at $139 found 1 day ago
Frontier Airlines
Tue, Oct 7 - Fri, Oct 10
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$187 Roundtrip, found 3 days ago
$187
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Oct 7 from Dallas-Fort Worth Intl. to Midway Intl., returning Fri, Oct 10, priced at $187 found 3 days ago
Frontier Airlines
Thu, Oct 9 - Sun, Oct 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$189 Roundtrip, found 5 days ago
$189
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Oct 9 from Los Angeles Intl. to Midway Intl., returning Sun, Oct 12, priced at $189 found 5 days ago
Contour Airlines
Fri, Oct 24 - Sun, Oct 26
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 4 hours ago
$189
Roundtrip
found 4 hours ago
Select Contour Airlines flight, departing Fri, Oct 24 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, Oct 26, priced at $189 found 4 hours ago
Delta
Sat, Sep 27 - Sat, Sep 27
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$195 Roundtrip, found 1 day ago
$195
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 27 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sat, Sep 27, priced at $195 found 1 day ago
Delta
Wed, Oct 1 - Sat, Oct 11
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 1 from Love Field to Midway Intl., returning Sat, Oct 11, priced at $197 found 1 day ago
Delta
Mon, Sep 15 - Wed, Sep 17
DAL
Love Field
ORD
O'Hare Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 15 from Love Field to O'Hare Intl., returning Wed, Sep 17, priced at $200 found 1 day ago
Alaska Airlines
Tue, Oct 21 - Wed, Oct 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 3 days ago
$216
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Tue, Oct 21 from Los Angeles Intl. to O'Hare Intl., returning Wed, Oct 22, priced at $216 found 3 days ago
Sun Country Airlines
Fri, Oct 31 - Mon, Nov 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$290 Roundtrip, found 10 hours ago
$290
Roundtrip
found 10 hours ago
Select Sun Country Airlines flight, departing Fri, Oct 31 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 3, priced at $290 found 10 hours ago
JetBlue Airways
Tue, Sep 9 - Sat, Sep 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$462 Roundtrip, found 1 day ago
$462
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 13, priced at $462 found 1 day 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.

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 September, 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 $87, 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 $87 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$63

Last Minute Hotel Deals in Chicago

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on Aug 20, 2025

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The Wade
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
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 ...
7.8/10 Good! (8,965 reviews)
"Family had a great stay."

Reviewed on Aug 21, 2025

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Congress Plaza 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
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,749 reviews)
"Very nice location. Close to redline (2 min walk) close to a lot of restaurants and convenient stores"

Reviewed on Aug 22, 2025

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Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,885 reviews)
"Beautiful unique hotel, friendly staff and quiet for people who need to rest!"

Reviewed on Aug 21, 2025

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Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (3,728 reviews)
"Stress"

Reviewed on Aug 21, 2025

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Hilton Garden Inn Chicago Downtown/Magnificent Mile
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,239 reviews)
"I loved how nice the hotel staff was."

Reviewed on Aug 21, 2025

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Freehand Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,669 reviews)
"What i liked was its location. In the middle of everything. But off the busy street. Restaurants & shopping a block away. What needs to be done is an upgrade to the bathroom. Wasn't bad , but tub/shower area need some attention."

Reviewed on Aug 20, 2025

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Hilton Chicago/Magnificent Mile Suites
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (3,614 reviews)
"Very clean and up to date location. Staff was very nice and check was smooth and easy"

Reviewed on Aug 21, 2025

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citizenM Chicago Downtown
See all 5,442 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

3.5 out of 5
2951 Touhy Ave, Elk Grove Village, IL
Stay at this 3.5-star business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
7.6/10 Good! (1,379 reviews)
"Property was fine, although vastly overpriced for the location and star level. Wish there had been a coffee maker in the room. It was fairly remote from dining options."

Reviewed on Aug 14, 2025

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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 E Grand Avenue, Bensenville, IL
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
7/10 Good! (1,027 reviews)
"Good"

Reviewed on Aug 19, 2025

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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
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! (2,013 reviews)
"Great, clean hotel. We took the shuttle to the airport to catch the train to Wrigley and they were super helpful!"

Reviewed on Aug 19, 2025

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Hampton Inn Chicago-O'Hare International Airport
Holiday Inn Chicago O'Hare Area by IHG

Holiday Inn Chicago O'Hare Area by IHG

3 out of 5
5615 North Cumberland Avenue, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
7.6/10 Good! (1,001 reviews)
"Property is convenient near the airport. The hotel also has a shuttle to the airport. The rooms are clean. I stay there once a year for my business trip."

Reviewed on Aug 16, 2025

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Holiday Inn Chicago O'Hare Area by IHG
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

4.5 out of 5
5300 N River Rd, Rosemont, IL
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 ...
9.4/10 Exceptional! (1,874 reviews)
"Great"

Reviewed on Aug 20, 2025

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Loews Chicago O'Hare Hotel
Carlton Inn Midway

Carlton Inn Midway

2 out of 5
4944 S Archer Ave, Chicago, IL
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 ...
6.4/10 (1,000 reviews)
"Tight parking lot and not a great looking part of town. Our room was down a dark, exterior hall. Inside was great though. Lobby and staff was great and room was very clean and comfortable."

Reviewed on Aug 17, 2025

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Carlton Inn Midway
See all 5,442 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.