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Chicago

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Chicago Flights as Low as $179

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

Bargain Flight
Wed, Aug 19 - Sun, Aug 23
FSD
Sioux Falls Regional
ORD
O'Hare Intl.
$179 Roundtrip, found 1 hour ago
$179
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Wed, Aug 19 from Sioux Falls Regional to O'Hare Intl., returning Sun, Aug 23, priced at $179 found 1 hour ago
Bargain Flight
Fri, Sep 25 - Mon, Sep 28
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Fri, Sep 25 from Charlotte-Douglas Intl. to O'Hare Intl., returning Mon, Sep 28, priced at $183 found 3 days ago
Bargain Flight
Thu, Sep 24 - Sun, Sep 27
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$190 Roundtrip, found 3 days ago
$190
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Thu, Sep 24 from Charlotte-Douglas Intl. to O'Hare Intl., returning Sun, Sep 27, priced at $190 found 3 days ago
Bargain Flight
Fri, Sep 25 - Sun, Sep 27
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$191 Roundtrip, found 3 days ago
$191
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Fri, Sep 25 from Charlotte-Douglas Intl. to O'Hare Intl., returning Sun, Sep 27, priced at $191 found 3 days ago
Delta
Tue, Sep 22 - Tue, Sep 29
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 3 days ago
$193
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Sep 22 from Charlotte-Douglas Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $193 found 3 days ago
Delta
Wed, Aug 5 - Tue, Aug 25
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Aug 5 from Charlotte-Douglas Intl. to O'Hare Intl., returning Tue, Aug 25, priced at $197 found 4 days ago
Bargain Flight
Tue, Oct 20 - Wed, Oct 28
MSY
Louis Armstrong New Orleans Intl.
ORD
O'Hare Intl.
$206 Roundtrip, found 6 days ago
$206
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Tue, Oct 20 from Louis Armstrong New Orleans Intl. to O'Hare Intl., returning Wed, Oct 28, priced at $206 found 6 days ago
American Airlines
Thu, Aug 27 - Mon, Aug 31
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Aug 27 from Charlotte-Douglas Intl. to O'Hare Intl., returning Mon, Aug 31, priced at $209 found 2 days ago
Delta
Tue, Sep 22 - Sat, Sep 26
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$211 Roundtrip, found 3 days ago
$211
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Sep 22 from Charlotte-Douglas Intl. to O'Hare Intl., returning Sat, Sep 26, priced at $211 found 3 days ago
Bargain Flight
Fri, Jul 10 - Sun, Jul 12
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$212 Roundtrip, found 3 days ago
$212
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Fri, Jul 10 from Charlotte-Douglas Intl. to O'Hare Intl., returning Sun, Jul 12, priced at $212 found 3 days ago
Delta
Wed, Aug 5 - Thu, Aug 27
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 4 days ago
$216
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Aug 5 from Charlotte-Douglas Intl. to O'Hare Intl., returning Thu, Aug 27, priced at $216 found 4 days ago
Frontier Airlines
Tue, Oct 6 - Tue, Oct 27
MSY
Louis Armstrong New Orleans Intl.
ORD
O'Hare Intl.
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Oct 6 from Louis Armstrong New Orleans Intl. to O'Hare Intl., returning Tue, Oct 27, priced at $220 found 1 day ago
Frontier Airlines
Tue, Jul 21 - Tue, Jul 28
MSY
Louis Armstrong New Orleans Intl.
MDW
Midway Intl.
$236 Roundtrip, found 2 hours ago
$236
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Jul 21 from Louis Armstrong New Orleans Intl. to Midway Intl., returning Tue, Jul 28, priced at $236 found 2 hours ago
Frontier Airlines
Tue, Jul 14 - Thu, Jul 30
CLT
Charlotte-Douglas Intl.
MDW
Midway Intl.
$265 Roundtrip, found 19 hours ago
$265
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Tue, Jul 14 from Charlotte-Douglas Intl. to Midway Intl., returning Thu, Jul 30, priced at $265 found 19 hours ago
JetBlue Airways
Thu, Sep 24 - Sun, Sep 27
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$383 Roundtrip, found 3 days ago
$383
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Sep 24 from Charlotte-Douglas Intl. to O'Hare Intl., returning Sun, Sep 27, priced at $383 found 3 days ago
American Airlines
Tue, Jun 16 - Fri, Jun 19
CLT
Charlotte-Douglas Intl.
RFD
Greater Rockford
$386 Roundtrip, found 3 days ago
$386
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Jun 16 from Charlotte-Douglas Intl. to Greater Rockford, returning Fri, Jun 19, priced at $386 found 3 days 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 August, 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 10 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 $179, 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 $179 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$100

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! (10,263 reviews)
"Our stay here was fantastic! We needed up having a tornado warning and the staff were amazing at keeping everyone calm and happy! The hotel itself was beautiful and in a perfect location! Thank you so much for having us!"

Reviewed on Jun 13, 2026

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Congress Plaza Hotel
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,664 reviews)
"Overall stay was great with my brother. I will come back agin. Staff were helpful especially with our shuttle ride to the airport."

Reviewed on Jun 13, 2026

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Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,571 reviews)
"PERFECT!!!!! Had such a smooth stay! I had a 5 hour delayed flight and was stuck in Nashville. My bestfriend had already made it to Chicago and was at the hotel. I called the hotel and let them know the situation and they allowed her to check in and get comfortable in our room (which was very beautiful). ..."

Reviewed on Jun 13, 2026

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The Chicago Hotel Collection - Magnificent Mile
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! (2,341 reviews)
"Welcoming, helpful staff, Clean, quiet room, Lovely, comfortable Hilton bed. Outstanding fitness room with new Life Fitness equipment! Great breakfast and Honors benefits, Just steps to terminal and train service."

Reviewed on Jun 13, 2026

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Hilton Chicago O'Hare Airport
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,601 reviews)
"Very easy check in. Very clean. Staff were very helpful. Beds are super comfortable. Parking little hard, but across the street on corner there's a lot for 58 dollars overnight a s hotel charges 80 dollars a night."

Reviewed on Jun 13, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
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! (4,419 reviews)
"The entire staff was amazing!"

Reviewed on Jun 13, 2026

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Hilton Chicago/Magnificent Mile Suites
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (2,788 reviews)
"the only issue i had it was that they didn’t do room service in the room, no new towels , no toilet paper and stuff like that"

Reviewed on Jun 12, 2026

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Hotel Felix River North/Magnificent Mile
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our ...
9.2/10 Wonderful! (3,097 reviews)
"The pool was amazing. Food and drink at the restaurants was not amazing, especially for the price."

Reviewed on Jun 13, 2026

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InterContinental Chicago Magnificent Mile by IHG
See all 5,465 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! (1,729 reviews)
"Every staff member I encountered was wonderful, shuttle service was very convenient."

Reviewed on Jun 13, 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 ...
7.6/10 Good! (1,504 reviews)
"I enjoyed my stay in a clean room with friendly helpful staff! The breakfast is amazing! I also used the treadmill for a great workout!"

Reviewed on Jun 13, 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! (2,338 reviews)
"Hard to access from handicap parking"

Reviewed on Jun 13, 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! (1,022 reviews)
"The breakfast buffet was delicious and had a wide variety of options"

Reviewed on Jun 11, 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! (2,096 reviews)
"Great place to stay"

Reviewed on Jun 13, 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 (1,020 reviews)
"The website photos are straight up lies. The words that come to mind for the establishment are dilapidated, dank, poorly constructed, cheap. The ‘fitness center’ consists of two treadmills and a clearly broken cable machine (the cords were loosely strewn all over), half of the ‘breakfast’ was either ..."

Reviewed on Jun 12, 2026

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Carlton Inn Midway
See all 5,465 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.