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Chicago

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Chicago Flights as Low as $56

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

Frontier Airlines
Tue, Apr 21 - Tue, Apr 28
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$56 Roundtrip, found 8 hours ago
$56
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, Apr 21 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Apr 28, priced at $56 found 8 hours ago
Frontier Airlines
Tue, Apr 14 - Tue, Apr 28
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$63 Roundtrip, found 8 hours ago
$63
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, Apr 14 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Apr 28, priced at $63 found 8 hours ago
Spirit Airlines
Mon, Apr 13 - Thu, Apr 16
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$99 Roundtrip, found 22 hours ago
$99
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Mon, Apr 13 from Newark Liberty Intl. Airport to O'Hare Intl., returning Thu, Apr 16, priced at $99 found 22 hours ago
Frontier Airlines
Wed, May 6 - Sat, May 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$106 Roundtrip, found 1 day ago
$106
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 6 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 16, priced at $106 found 1 day ago
Frontier Airlines
Mon, Apr 20 - Thu, May 7
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$133 Roundtrip, found 3 hours ago
$133
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, Apr 20 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, May 7, priced at $133 found 3 hours ago
Frontier Airlines
Wed, Apr 22 - Wed, Apr 29
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$140 Roundtrip, found 3 hours ago
$140
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Wed, Apr 29, priced at $140 found 3 hours ago
American Airlines
Wed, Apr 15 - Tue, Apr 21
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Apr 15 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Apr 21, priced at $187 found 1 day ago
United
Wed, Jun 10 - Wed, Jun 17
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$190 Roundtrip, found 20 hours ago
$190
Roundtrip
found 20 hours ago
Select United flight, departing Wed, Jun 10 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Jun 17, priced at $190 found 20 hours ago
Frontier Airlines
Thu, Apr 16 - Tue, Apr 21
LAX
Los Angeles Intl.
MDW
Midway Intl.
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Los Angeles Intl. to Midway Intl., returning Tue, Apr 21, priced at $203 found 1 day ago
Delta
Sat, Apr 18 - Fri, May 1
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$204 Roundtrip, found 8 hours ago
$204
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Apr 18 from Newark Liberty Intl. Airport to Midway Intl., returning Fri, May 1, priced at $204 found 8 hours ago
American Airlines
Tue, May 26 - Tue, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
RFD
Greater Rockford
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, May 26 from Baltimore Washington Intl. Thurgood Marshall to Greater Rockford, returning Tue, Jun 2, priced at $232 found 1 day ago
American Airlines
Thu, Jul 30 - Sat, Aug 8
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$310 Roundtrip, found 1 day ago
$310
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jul 30 from Newark Liberty Intl. Airport to Greater Rockford, returning Sat, Aug 8, priced at $310 found 1 day ago
Alaska Airlines
Wed, Apr 22 - Tue, May 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$313 Roundtrip, found 1 hour ago
$313
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Wed, Apr 22 from Los Angeles Intl. to O'Hare Intl., returning Tue, May 5, priced at $313 found 1 hour ago
Sun Country Airlines
Mon, Apr 20 - Thu, May 7
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$385 Roundtrip, found 3 hours ago
$385
Roundtrip
found 3 hours ago
Select Sun Country Airlines flight, departing Mon, Apr 20 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, May 7, priced at $385 found 3 hours ago
JetBlue Airways
Tue, Apr 21 - Sat, May 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$398 Roundtrip, found 10 hours ago
$398
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Tue, Apr 21 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 2, priced at $398 found 10 hours ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$416 Roundtrip, found 1 hour ago
$416
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $416 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 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 $56, 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 $56 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$56

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! (9,999 reviews)
I was very disappointed with my stay at the Congress Hotel. The room was in clear need of maintenance and updating. There were cracked tiles and damaged drywall, and the overall condition felt worn and neglected. The heating and air conditioning unit did not function properly, which made the room ...

Reviewed on Mar 28, 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! (4,004 reviews)
Clean and well kept overall. Great Australian restaurant in the lobby.

Reviewed on Mar 28, 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! (5,790 reviews)
Great spot in the shopping district. Good breakfast and nice to have the snacks and drinks for the happy hour time.

Reviewed on Mar 28, 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! (3,653 reviews)
This is an amazing hotel!!! I have stayed in hotels all over the world and this is in the top 10!!! Breakfast was amazing and the room is perfect. Staff went above and beyond to make you feel welcome.

Reviewed on Mar 28, 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! (2,238 reviews)
Everything was clean and the staff was very friendly and helpful!

Reviewed on Mar 25, 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! (1,758 reviews)
No water view

Reviewed on Mar 27, 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)
Staff is not accommodating.

Reviewed on Mar 28, 2026

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Aloft Chicago Mag Mile
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the ...
9/10 Wonderful! (3,227 reviews)
Some issues with the room and internet, had to switch rooms. The second room had a malfunctioning toilet fill valve, it would shut off due to friction, requiring me to pull the lid and jiggle it to fill. Some outlet's didn't work. Low hanging fruit that can be attended to can go a long way. Staff ...

Reviewed on Mar 27, 2026

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Swissotel - Chicago
See all 5,527 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! (1,633 reviews)
I was very disappointed with my stay. I specifically booked a king size bed but the room I was given was significantly smaller than what was advertised. To make matters worse, the room felt completely rundown. The furnishings were worn out, and it clearly hasn't been properly maintained in some time. ...

Reviewed on Mar 24, 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! (1,321 reviews)
Hotel was clean and friendly staff. Breakfast was very limited.

Reviewed on Mar 28, 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! (2,251 reviews)
Such friendly staff. Thats a relief when traveling. Love the 530am start to the breakfast buffet. Rooms are cozy. Close to the airport and includes a speedy shuttle. We frequent this spot amd have no need to try anywhere else.

Reviewed on Mar 26, 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! (1,001 reviews)
24 hr shuttle to the airport

Reviewed on Mar 24, 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)
Excellent

Reviewed on Mar 26, 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 ...
Get rates
Carlton Inn Midway
See all 5,527 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.