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Chicago

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Chicago Flights as Low as $59

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

Spirit Airlines
Tue, Apr 21 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$59 Roundtrip, found 1 hour ago
$59
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Apr 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, May 2, priced at $59 found 1 hour ago
Frontier Airlines
Sat, Apr 18 - Mon, Apr 20
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$72 Roundtrip, found 20 hours ago
$72
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Sat, Apr 18 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Apr 20, priced at $72 found 20 hours ago
Spirit Airlines
Tue, Apr 28 - Wed, Apr 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 6 hours ago
$73
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Apr 28 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Apr 29, priced at $73 found 6 hours ago
Frontier Airlines
Tue, May 5 - Tue, May 19
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$79 Roundtrip, found 1 day ago
$79
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 5 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, May 19, priced at $79 found 1 day ago
Frontier Airlines
Thu, Apr 9 - Thu, Apr 23
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$115 Roundtrip, found 3 hours ago
$115
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Apr 9 from Charlotte-Douglas Intl. to O'Hare Intl., returning Thu, Apr 23, priced at $115 found 3 hours ago
Bargain Flight
Sun, Jun 14 - Thu, Jun 18
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sun, Jun 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Jun 18, priced at $167 found 2 days ago
American Airlines
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$195 Roundtrip, found 1 hour ago
$195
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $195 found 1 hour ago
Delta
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$195 Roundtrip, found 1 hour ago
$195
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $195 found 1 hour ago
Frontier Airlines
Fri, Apr 10 - Mon, Apr 13
CLT
Charlotte-Douglas Intl.
MDW
Midway Intl.
$205 Roundtrip, found 4 days ago
$205
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Apr 10 from Charlotte-Douglas Intl. to Midway Intl., returning Mon, Apr 13, priced at $205 found 4 days ago
Contour Airlines
Fri, Jun 19 - Mon, Jun 22
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Fri, Jun 19 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Jun 22, priced at $209 found 2 days ago
Delta
Sat, May 9 - Tue, May 12
DAL
Love Field
MDW
Midway Intl.
$222 Roundtrip, found 14 hours ago
$222
Roundtrip
found 14 hours ago
Select Delta flight, departing Sat, May 9 from Love Field to Midway Intl., returning Tue, May 12, priced at $222 found 14 hours ago
Delta
Tue, May 12 - Sat, May 16
DAL
Love Field
ORD
O'Hare Intl.
$222 Roundtrip, found 5 hours ago
$222
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, May 12 from Love Field to O'Hare Intl., returning Sat, May 16, priced at $222 found 5 hours ago
American Airlines
Mon, Apr 27 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$248 Roundtrip, found 4 hours ago
$248
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Mon, Apr 27 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, May 1, priced at $248 found 4 hours ago
American Airlines
Fri, May 15 - Mon, May 18
CLT
Charlotte-Douglas Intl.
RFD
Greater Rockford
$271 Roundtrip, found 1 day ago
$271
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, May 15 from Charlotte-Douglas Intl. to Greater Rockford, returning Mon, May 18, priced at $271 found 1 day ago
American Airlines
Fri, Apr 10 - Tue, Apr 14
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$377 Roundtrip, found 6 hours ago
$377
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Fri, Apr 10 from Dallas-Fort Worth Intl. to Greater Rockford, returning Tue, Apr 14, priced at $377 found 6 hours ago
JetBlue Airways
Wed, May 6 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$378 Roundtrip, found 6 hours ago
$378
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Wed, May 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 12, priced at $378 found 6 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.

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 April, 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 15 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 $59, 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 $59 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
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
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 ...
8/10 Very Good! (10,013 reviews)
Stayed here several times. This is the only place I stay in Chicago and always a five star experience!

Reviewed on Apr 3, 2026

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Congress Plaza Hotel
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 ...
9/10 Wonderful! (4,043 reviews)
Room was nicely appointed, clean and comfortable bed and pillows. One downside was the room would not cool down past 73 degrees. It was hot and made for pretty uncomfortable sleeping conditions. Would like to stay again but they need to get the air figured out.

Reviewed on Apr 3, 2026

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Hilton Chicago/Magnificent Mile Suites
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 hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,813 reviews)
Good service clean place

Reviewed on Apr 3, 2026

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Embassy Suites by Hilton Chicago Downtown River North
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (3,713 reviews)
The breakfast was very good. They had a great selection of food

Reviewed on Apr 3, 2026

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Hotel Riu Plaza Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,242 reviews)
Convenience

Reviewed on Apr 3, 2026

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Hilton Chicago O'Hare Airport
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,769 reviews)
Clean room, great view, close to lake! Loved!

Reviewed on Apr 3, 2026

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The Wade
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (3,157 reviews)
We pre-purchased the breakfast, but the options that they had were limited and overpriced. Everything was premade and frozen.. If we knew beforehand what was offered, we wouldn’t have purchased that.

Reviewed on Apr 2, 2026

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Aloft Chicago Mag 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 ...
9.4/10 Exceptional! (3,475 reviews)
This hotel is great! Great location, great staff.

Reviewed on Apr 3, 2026

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Hyatt Regency Chicago
See all 5,628 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 ...
7.6/10 Good! (1,631 reviews)
Very good

Reviewed on Apr 2, 2026

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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
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 ...
7.4/10 Good! (1,331 reviews)
Great experience all around!

Reviewed on Apr 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 ...
9.2/10 Wonderful! (2,254 reviews)
Everything was great

Reviewed on Apr 3, 2026

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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 ...
8.2/10 Very Good! (1,004 reviews)
Everything was wonderful. Breakfast, Parking the room. It was our first time and we will definitely be staying here again.

Reviewed on Apr 3, 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 ...
9.4/10 Exceptional! (2,003 reviews)
İt was a pleasant stay

Reviewed on Apr 3, 2026

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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 ...
6.2/10 (1,000 reviews)
Dirty!! no bar soap. Bathroom was dirty, shower tub was clogged as you showered, carpet was dirty, on the 2nd day we asked them to tidy up the room, but the cleaning lady did not even step in the room.

Reviewed on Mar 29, 2026

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Carlton Inn Midway
See all 5,628 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.