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Chicago

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Chicago Flights as Low as $100

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

Frontier Airlines
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 1 hour ago
$100
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $100 found 1 hour ago
Frontier Airlines
Sat, Nov 14 - Mon, Nov 16
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$156 Roundtrip, found 1 hour ago
$156
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Nov 14 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Nov 16, priced at $156 found 1 hour ago
Frontier Airlines
Tue, Oct 27 - Tue, Nov 10
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$161 Roundtrip, found 19 hours ago
$161
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Tue, Oct 27 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Nov 10, priced at $161 found 19 hours ago
Frontier Airlines
Tue, Oct 20 - Fri, Oct 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 3 days ago
$172
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Oct 20 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Fri, Oct 30, priced at $172 found 3 days ago
Bargain Flight
Wed, Oct 21 - Thu, Oct 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$174 Roundtrip, found 1 hour ago
$174
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Wed, Oct 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Oct 29, priced at $174 found 1 hour ago
Delta
Wed, Nov 11 - Wed, Nov 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$194 Roundtrip, found 2 days ago
$194
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Nov 11 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $194 found 2 days ago
Delta
Fri, Nov 13 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Nov 13 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 13, priced at $197 found 2 days ago
American Airlines
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$200 Roundtrip, found 1 hour ago
$200
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $200 found 1 hour ago
Southwest Airlines
Mon, Nov 9 - Fri, Nov 13
LAX
Los Angeles Intl.
MDW
Midway Intl.
$200 Roundtrip, found 11 hours ago
$200
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Mon, Nov 9 from Los Angeles Intl. to Midway Intl., returning Fri, Nov 13, priced at $200 found 11 hours ago
Frontier Airlines
Mon, Dec 21 - Mon, Jan 11
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$224 Roundtrip, found 16 hours ago
$224
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Mon, Dec 21 from Sky Harbor Intl. to O'Hare Intl., returning Mon, Jan 11, priced at $224 found 16 hours ago
Bargain Flight
Mon, Oct 26 - Thu, Oct 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$240 Roundtrip, found 2 hours ago
$240
Roundtrip
found 2 hours ago
Select Bargain Flight flight, departing Mon, Oct 26 from Los Angeles Intl. to O'Hare Intl., returning Thu, Oct 29, priced at $240 found 2 hours ago
Contour Airlines
Sat, Oct 17 - Wed, Oct 21
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$283 Roundtrip, found 2 days ago
$283
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Sat, Oct 17 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Oct 21, priced at $283 found 2 days ago
JetBlue Airways
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$295 Roundtrip, found 1 hour ago
$295
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $295 found 1 hour ago
Delta
Sat, Nov 7 - Tue, Nov 17
DAL
Love Field
ORD
O'Hare Intl.
$297 Roundtrip, found 2 days ago
$297
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Nov 7 from Love Field to O'Hare Intl., returning Tue, Nov 17, priced at $297 found 2 days ago
Southwest Airlines
Fri, Nov 6 - Mon, Nov 9
DAL
Love Field
MDW
Midway Intl.
$321 Roundtrip, found 2 days ago
$321
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Nov 6 from Love Field to Midway Intl., returning Mon, Nov 9, priced at $321 found 2 days ago
Southwest Airlines
Mon, Dec 21 - Thu, Dec 24
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$329 Roundtrip, found 1 hour ago
$329
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Mon, Dec 21 from Sky Harbor Intl. to Midway Intl., returning Thu, Dec 24, priced at $329 found 1 hour 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 December, 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 14 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 $100, 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 $100 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$99

Last Minute Hotel Deals in Chicago

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 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
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Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
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River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (2,400 reviews)
"The hotel was a very convenient location from downtown and Lake Michigan. Definitely one of the better breakfasts I've had recently and the pricing sits just right for the amenities and convenience this hotel offers"

Reviewed on Oct 3, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
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The Chicago Hotel Collection - Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
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Hilton Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (2,688 reviews)
"The staff was helpful for the most part, but the woman monitoring the breakfast was not. Another woman and I were looking for her to refill the flatware as we both had yogurt. When we asked her, she walked past the station and into the kitchen where we could easily see her chatting with the cook. ..."

Reviewed on Oct 2, 2026

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Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Book a stay at this 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 ...
9/10 Wonderful! (3,946 reviews)
"Slight wear and tear on the furniture dates the place and I wish the rooms were brighter, but excellent location and great value. Loved the shower!"

Reviewed on Oct 2, 2026

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Eurostars Magnificent Mile
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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Hyatt Regency Chicago
See all 5,458 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
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 ...
Get rates
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
Book a stay at this golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.6/10 Good! (1,809 reviews)
"Overall decent place by the airport to stay a few nights. Pros: - Free breakfast (sausages, eggs, waffles, etc.) - Free airport shuttle (although you have to call them when you land to get a tracking link) - (mostly) clean and comfortable rooms and pool & hot tub Cons: - Rooms and carpets need deeper ..."

Reviewed on Oct 2, 2026

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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 ...
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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
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
8.4/10 Very Good! (1,002 reviews)
"The staff was most helpful with our late arrival. My husband needed wheelchair assistance and the hotel had one for our use. They also commented on our anniversary and surprised us by comping our breakfast. We have stayed at, and will return to this property. It is well maintained, has a restaurant/sports ..."

Reviewed on Oct 2, 2026

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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
Book a stay at this luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful ...
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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 ...
6/10 (1,005 reviews)
"Please do not chose it if with kids, seniors and decent people. Plain utilitarian and we picked as it was the only one on walking distance from a gathering we had in Midway. Never again. The smell of marijuana in the room and everywhere you walked within property grounds, is terrible. The room needs ..."

Reviewed on Oct 2, 2026

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Carlton Inn Midway
See all 5,458 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.