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Chicago

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Chicago Flights as Low as $68

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

Frontier Airlines
Sat, Apr 25 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Apr 25 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, May 2, priced at $68 just found
Spirit Airlines
Wed, Apr 29 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 2 hours ago
$73
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, Apr 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, May 2, priced at $73 found 2 hours ago
Frontier Airlines
Wed, Apr 29 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$75 Roundtrip, found 2 hours ago
$75
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Apr 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, May 2, priced at $75 found 2 hours ago
Frontier Airlines
Wed, Apr 29 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, found 2 hours ago
$76
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Apr 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, May 2, priced at $76 found 2 hours ago
Spirit Airlines
Sat, Apr 25 - Tue, Apr 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$93 Roundtrip, found 1 day ago
$93
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Apr 25 from Los Angeles Intl. to O'Hare Intl., returning Tue, Apr 28, priced at $93 found 1 day ago
American Airlines
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$195 Roundtrip, found 2 hours ago
$195
Roundtrip
found 2 hours 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 2 hours ago
Delta
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$195 Roundtrip, found 2 hours ago
$195
Roundtrip
found 2 hours 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 2 hours ago
United
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$201 Roundtrip, found 2 hours ago
$201
Roundtrip
found 2 hours ago
Select United flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $201 found 2 hours ago
Frontier Airlines
Fri, Apr 24 - Sat, May 2
LAX
Los Angeles Intl.
MDW
Midway Intl.
$209 Roundtrip, found 7 hours ago
$209
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Fri, Apr 24 from Los Angeles Intl. to Midway Intl., returning Sat, May 2, priced at $209 found 7 hours ago
Delta
Sat, May 9 - Tue, May 12
DAL
Love Field
MDW
Midway Intl.
$222 Roundtrip, found 20 hours ago
$222
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, May 9 from Love Field to Midway Intl., returning Tue, May 12, priced at $222 found 20 hours ago
Delta
Tue, May 12 - Sat, May 16
DAL
Love Field
ORD
O'Hare Intl.
$241 Roundtrip, just found
$241
Roundtrip
just found
Select Delta flight, departing Tue, May 12 from Love Field to O'Hare Intl., returning Sat, May 16, priced at $241 just found
American Airlines
Mon, Apr 27 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$305 Roundtrip, found 1 hour ago
$305
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Mon, Apr 27 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, May 1, priced at $305 found 1 hour ago
American Airlines
Mon, May 25 - Tue, May 26
LAX
Los Angeles Intl.
RFD
Greater Rockford
$335 Roundtrip, found 4 hours ago
$335
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Mon, May 25 from Los Angeles Intl. to Greater Rockford, returning Tue, May 26, priced at $335 found 4 hours ago
Alaska Airlines
Wed, May 6 - Thu, May 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$345 Roundtrip, found 11 hours ago
$345
Roundtrip
found 11 hours ago
Select Alaska Airlines flight, departing Wed, May 6 from Los Angeles Intl. to O'Hare Intl., returning Thu, May 7, priced at $345 found 11 hours ago
JetBlue Airways
Wed, May 6 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$375 Roundtrip, found 18 hours ago
$375
Roundtrip
found 18 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 $375 found 18 hours ago
Sun Country Airlines
Sun, May 17 - Thu, May 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$552 Roundtrip, found 5 hours ago
$552
Roundtrip
found 5 hours ago
Select Sun Country Airlines flight, departing Sun, May 17 from Los Angeles Intl. to O'Hare Intl., returning Thu, May 21, priced at $552 found 5 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 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 $68, 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 $68 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$68

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! (10,080 reviews)
Parking was terrible and extremely expensive

Reviewed on Apr 10, 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! (4,099 reviews)
Recommend packing light if you self-park and walk to the hotel!

Reviewed on Apr 11, 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! (5,833 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly. We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request ...

Reviewed on Apr 9, 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! (3,787 reviews)
The place was beautiful. Breakfast was lovely and I enjoyed everything.

Reviewed on Apr 10, 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! (2,263 reviews)
I keep coming back to this hotel because of the location, but honestly it is a disappointment every time. The rooms are dated, the carpets are old and worn, and the elevators are slow. The door to my room was broken, so every time I wanted to leave for food or go to gym, I had to go downstairs, alert ...

Reviewed on Apr 9, 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! (1,786 reviews)
Clean room and well staffed, would 100% coma back

Reviewed on Apr 7, 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! (3,167 reviews)
Clean room.

Reviewed on Apr 10, 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! (3,492 reviews)
Clean room

Reviewed on Apr 10, 2026

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Hyatt Regency Chicago
See all 5,589 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! (1,640 reviews)
Quick check in. Nice pool.

Reviewed on Apr 10, 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! (1,341 reviews)
I just prefer to eat in my room sometimes...

Reviewed on Apr 10, 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! (2,256 reviews)
Location is great. It is on a busy and loud street of course. Couldn't hear any airplane traffic. The room we got was with 2 queen beds, spacious, with mini fridge (no freezer), microwave, wardrobe with mirror, another big mirror, even night light in the bathroom, which I love. Breakfast was good, ...

Reviewed on Apr 8, 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)
Didn’t like the way they treat us

Reviewed on Apr 9, 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! (2,018 reviews)
clean room, great food and staff was nice

Reviewed on Apr 9, 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 (1,001 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 5,589 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.