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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 4 hours ago
$56
Roundtrip
found 4 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 4 hours ago
Frontier Airlines
Tue, Apr 21 - Thu, Apr 30
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$95 Roundtrip, found 6 days ago
$95
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Apr 21 from Newark Liberty Intl. Airport to Midway Intl., returning Thu, Apr 30, priced at $95 found 6 days ago
Frontier Airlines
Sat, Apr 25 - Tue, Apr 28
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$97 Roundtrip, found 6 days ago
$97
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Apr 25 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Apr 28, priced at $97 found 6 days ago
Spirit Airlines
Mon, Apr 13 - Thu, Apr 16
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$99 Roundtrip, found 4 hours ago
$99
Roundtrip
found 4 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 4 hours ago
Frontier Airlines
Wed, May 6 - Sat, May 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$106 Roundtrip, found 16 hours ago
$106
Roundtrip
found 16 hours 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 16 hours ago
Frontier Airlines
Sat, May 23 - Sat, May 30
AUS
Austin-Bergstrom Intl.
MDW
Midway Intl.
$176 Roundtrip, found 23 hours ago
$176
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sat, May 23 from Austin-Bergstrom Intl. to Midway Intl., returning Sat, May 30, priced at $176 found 23 hours ago
Frontier Airlines
Tue, Apr 7 - Mon, Apr 13
AUS
Austin-Bergstrom Intl.
ORD
O'Hare Intl.
$181 Roundtrip, found 2 days ago
$181
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Apr 7 from Austin-Bergstrom Intl. to O'Hare Intl., returning Mon, Apr 13, priced at $181 found 2 days ago
Frontier Airlines
Wed, Apr 15 - Tue, Apr 21
LAX
Los Angeles Intl.
MDW
Midway Intl.
$185 Roundtrip, found 1 hour ago
$185
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Apr 15 from Los Angeles Intl. to Midway Intl., returning Tue, Apr 21, priced at $185 found 1 hour ago
American Airlines
Wed, Apr 15 - Tue, Apr 21
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$187 Roundtrip, found 14 hours ago
$187
Roundtrip
found 14 hours 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 14 hours ago
United
Wed, Jun 10 - Wed, Jun 17
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$190 Roundtrip, found 2 hours ago
$190
Roundtrip
found 2 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 2 hours ago
Delta
Tue, Apr 21 - Tue, Apr 28
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$204 Roundtrip, found 4 hours ago
$204
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Apr 21 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Apr 28, priced at $204 found 4 hours ago
American Airlines
Thu, Jul 30 - Sat, Aug 8
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$310 Roundtrip, found 14 hours ago
$310
Roundtrip
found 14 hours 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 14 hours ago
Alaska Airlines
Wed, Apr 22 - Wed, May 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$313 Roundtrip, found 4 hours ago
$313
Roundtrip
found 4 hours ago
Select Alaska Airlines flight, departing Wed, Apr 22 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 6, priced at $313 found 4 hours ago
JetBlue Airways
Tue, Apr 21 - Wed, May 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$345 Roundtrip, found 7 hours ago
$345
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Tue, Apr 21 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 6, priced at $345 found 7 hours ago
American Airlines
Fri, Sep 4 - Sat, Sep 5
AUS
Austin-Bergstrom Intl.
RFD
Greater Rockford
$373 Roundtrip, found 2 days ago
$373
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Sep 4 from Austin-Bergstrom Intl. to Greater Rockford, returning Sat, Sep 5, priced at $373 found 2 days ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$532 Roundtrip, found 4 hours ago
$532
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $532 found 4 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 $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! (9,995 reviews)
Not much staff was apparent on the main floor throughout my stay. My initial encounter at check-in was with an unhelpful person but most of the staff was excellent. Instructions for the in-room coffee machine were not provided and I wasted the only coffee trying to work it. Walls were thin and adjacent ...

Reviewed on Mar 27, 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! (3,993 reviews)
We had booked the lake view king suite room which the view was not great. When we got into the room it was very hot and we tried to turn the ac on but the air blowing out was still hot. Definitely would not book there again

Reviewed on Mar 27, 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! (5,786 reviews)
The staff was very friendly and helpful.

Reviewed on Mar 27, 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! (3,647 reviews)
Clean room, gray lobby and nice bar with excellent bartender, breakfast was very good !

Reviewed on Mar 27, 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! (2,235 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! (1,757 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! (3,155 reviews)
Amazing hotel and rooms smelled so clean. Breakfast was good quality! Definitely will be staying here again

Reviewed on Mar 27, 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! (3,226 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! (1,319 reviews)
Shuttle made us wait 45 past the time posted. Told us they were there at the airport when they weren’t. Rooms were dirty. Bathrooms dirty. Not maintained. Staff couldn’t be bothered to help. Loud. Couldn’t sleep from the noise from other rooms.

Reviewed on Mar 27, 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! (2,250 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! (2,002 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 ...
6.2/10 (1,000 reviews)
El cuarto olía mucho a cigarro y según era no fumar.

Reviewed on Mar 23, 2026

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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.