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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.

Spirit Airlines
Mon, Mar 9 - Tue, Mar 10
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$56 Roundtrip, found 21 hours ago
$56
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Mon, Mar 9 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Mar 10, priced at $56 found 21 hours ago
Frontier Airlines
Mon, Apr 27 - Tue, May 12
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$66 Roundtrip, found 13 hours ago
$66
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Mon, Apr 27 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, May 12, priced at $66 found 13 hours ago
Frontier Airlines
Sun, Mar 8 - Thu, Mar 26
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$68 Roundtrip, found 12 hours ago
$68
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sun, Mar 8 from Newark Liberty Intl. Airport to Midway Intl., returning Thu, Mar 26, priced at $68 found 12 hours ago
Spirit Airlines
Fri, Mar 6 - Wed, Mar 18
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$70 Roundtrip, found 1 day ago
$70
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Mar 6 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Mar 18, priced at $70 found 1 day ago
Spirit Airlines
Tue, Mar 10 - Tue, Mar 10
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$73 Roundtrip, found 3 days ago
$73
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Mar 10 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Mar 10, priced at $73 found 3 days ago
Spirit Airlines
Fri, Mar 6 - Sat, Mar 7
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$77 Roundtrip, found 1 day ago
$77
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Mar 6 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Mar 7, priced at $77 found 1 day ago
Frontier Airlines
Fri, Feb 13 - Mon, Mar 2
PHL
Philadelphia Intl.
ORD
O'Hare Intl.
$94 Roundtrip, found 5 days ago
$94
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Feb 13 from Philadelphia Intl. to O'Hare Intl., returning Mon, Mar 2, priced at $94 found 5 days ago
United
Sat, May 2 - Fri, May 8
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Select United flight, departing Sat, May 2 from Newark Liberty Intl. Airport to O'Hare Intl., returning Fri, May 8, priced at $137 found 6 days ago
American Airlines
Mon, Mar 9 - Tue, Mar 10
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$152 Roundtrip, found 21 hours ago
$152
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Mon, Mar 9 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Mar 10, priced at $152 found 21 hours ago
Frontier Airlines
Sat, Feb 21 - Sat, Feb 28
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$154 Roundtrip, found 2 days ago
$154
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Feb 21 from Hopkins Intl. to O'Hare Intl., returning Sat, Feb 28, priced at $154 found 2 days ago
Frontier Airlines
Wed, Mar 4 - Tue, Mar 10
TTN
Mercer
ORD
O'Hare Intl.
$159 Roundtrip, found 6 days ago
$159
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Mar 4 from Mercer to O'Hare Intl., returning Tue, Mar 10, priced at $159 found 6 days ago
Frontier Airlines
Tue, Feb 24 - Sat, Feb 28
PHL
Philadelphia Intl.
MDW
Midway Intl.
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Feb 24 from Philadelphia Intl. to Midway Intl., returning Sat, Feb 28, priced at $164 found 1 day ago
Delta
Tue, May 5 - Tue, May 5
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, May 5 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, May 5, priced at $177 found 6 days ago
Frontier Airlines
Fri, Feb 20 - Sat, Feb 28
TTN
Mercer
MDW
Midway Intl.
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Feb 20 from Mercer to Midway Intl., returning Sat, Feb 28, priced at $179 found 1 day ago
JetBlue Airways
Mon, Mar 30 - Tue, Apr 14
PHL
Philadelphia Intl.
ORD
O'Hare Intl.
$228 Roundtrip, found 4 days ago
$228
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Mar 30 from Philadelphia Intl. to O'Hare Intl., returning Tue, Apr 14, priced at $228 found 4 days ago
Frontier Airlines
Sat, Feb 14 - Thu, Feb 19
CLE
Hopkins Intl.
MDW
Midway Intl.
$286 Roundtrip, found 8 hours ago
$286
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Feb 14 from Hopkins Intl. to Midway Intl., returning Thu, Feb 19, priced at $286 found 8 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 March, 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
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$55

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! (9,859 reviews)
Great location, clean room, but the walls between rooms are paper thin - could hear the tv and conversations next door.

Reviewed on Feb 6, 2026

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Congress Plaza Hotel
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 ...
8.2/10 Very Good! (2,211 reviews)
Easy booking, they let me check in early which I needed it. Friendly staff, nice bed, good shower pressure, clean room. Just need some updating to make it brighter room. Overall satisfied with my stay.

Reviewed on Feb 2, 2026

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Hilton Chicago O'Hare Airport
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 ...
8.4/10 Very Good! (5,637 reviews)
Yes room was spotless

Reviewed on Feb 4, 2026

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Embassy Suites by Hilton Chicago Downtown River North
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 ...
8.4/10 Very Good! (2,609 reviews)
Great location and great hotel!

Reviewed on Feb 3, 2026

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Hilton Chicago
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 ...
9.2/10 Wonderful! (3,303 reviews)
Room was brilliant and always very clean, staff was excellent very accommodating and very well mannered.

Reviewed on Feb 7, 2026

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Hotel Riu Plaza Chicago
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! (3,073 reviews)
Great room and location

Reviewed on Feb 7, 2026

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Aloft Chicago Mag Mile
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 ...
8.8/10 Excellent! (3,782 reviews)
Such great service, room was clean, and hotel staff were amazing! 10/10 recommend and will be staying here again when we come back!

Reviewed on Feb 4, 2026

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Hilton Chicago/Magnificent Mile Suites
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the ...
8.6/10 Excellent! (2,292 reviews)
The staff was amazing and so nice! They have a small Starbucks within the building. The hotel surrounds everything you can think of!

Reviewed on Feb 6, 2026

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DoubleTree by Hilton Chicago - Magnificent Mile
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! (1,611 reviews)
A little outdated but it was clean and well maintained.

Reviewed on Feb 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 ...
7.2/10 Good! (1,261 reviews)
A little dated but overall ok hotel.

Reviewed on Feb 7, 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! (2,212 reviews)
I recently visited Chicago from Atlanta to spend Saturday with my grandson who goes to college outside of Chicago. Staying at this Hampton Inn made the trip so easy. The staff was extremely courteous, especially the front desk. The room was spotless. The breakfast was very good. The easiest part ...

Reviewed on Feb 6, 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 ...
8/10 Very Good! (1,002 reviews)
Staff was wonderful. Hotel clean

Reviewed on Jan 31, 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! (1,953 reviews)
Last minute booking and it was terrific. Beautiful property and the staff was exceptional, accommodating a few of our requests. Thank you!

Reviewed on Feb 5, 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 (1,002 reviews)
The rooms are clean, the hot water takes about three minutes to get hot, but it did get very hot. Also water $1 pop $2 that was great.

Reviewed on Jan 28, 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.