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Chicago

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Chicago Flights as Low as $145

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

Frontier Airlines
Fri, Oct 9 - Mon, Oct 19
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$145 Roundtrip, found 4 hours ago
$145
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, Oct 9 from Sky Harbor Intl. to O'Hare Intl., returning Mon, Oct 19, priced at $145 found 4 hours ago
Frontier Airlines
Thu, Nov 12 - Sat, Nov 14
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$148 Roundtrip, found 3 hours ago
$148
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Nov 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Nov 14, priced at $148 found 3 hours ago
Bargain Flight
Tue, Nov 17 - Tue, Dec 1
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Nov 17 from Raleigh - Durham Intl. to O'Hare Intl., returning Tue, Dec 1, priced at $183 found 1 day ago
Frontier Airlines
Mon, Sep 28 - Tue, Sep 29
RDU
Raleigh - Durham Intl.
MDW
Midway Intl.
$222 Roundtrip, found 4 hours ago
$222
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Raleigh - Durham Intl. to Midway Intl., returning Tue, Sep 29, priced at $222 found 4 hours ago
Frontier Airlines
Sun, Sep 6 - Fri, Sep 18
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$230 Roundtrip, found 4 days ago
$230
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Sep 6 from Dallas-Fort Worth Intl. to Midway Intl., returning Fri, Sep 18, priced at $230 found 4 days ago
American Airlines
Mon, Sep 28 - Thu, Oct 1
RDU
Raleigh - Durham Intl.
RFD
Greater Rockford
$256 Roundtrip, found 10 hours ago
$256
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Mon, Sep 28 from Raleigh - Durham Intl. to Greater Rockford, returning Thu, Oct 1, priced at $256 found 10 hours ago
Delta
Tue, Dec 15 - Thu, Dec 17
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$277 Roundtrip, found 23 hours ago
$277
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Dec 15 from Raleigh - Durham Intl. to O'Hare Intl., returning Thu, Dec 17, priced at $277 found 23 hours ago
Contour Airlines
Fri, Sep 11 - Mon, Sep 14
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$303 Roundtrip, found 3 hours ago
$303
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Fri, Sep 11 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Sep 14, priced at $303 found 3 hours ago
Alaska Airlines
Thu, Nov 19 - Wed, Dec 9
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$306 Roundtrip, found 7 hours ago
$306
Roundtrip
found 7 hours ago
Select Alaska Airlines flight, departing Thu, Nov 19 from Sky Harbor Intl. to O'Hare Intl., returning Wed, Dec 9, priced at $306 found 7 hours ago
Southwest Airlines
Fri, Oct 16 - Mon, Oct 19
DAL
Love Field
MDW
Midway Intl.
$315 Roundtrip, found 9 hours ago
$315
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Fri, Oct 16 from Love Field to Midway Intl., returning Mon, Oct 19, priced at $315 found 9 hours ago
Southwest Airlines
Fri, Oct 2 - Mon, Oct 5
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$323 Roundtrip, found 4 hours ago
$323
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Fri, Oct 2 from Sky Harbor Intl. to Midway Intl., returning Mon, Oct 5, priced at $323 found 4 hours ago
Delta
Fri, Oct 30 - Tue, Nov 17
DAL
Love Field
ORD
O'Hare Intl.
$334 Roundtrip, found 1 day ago
$334
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 30 from Love Field to O'Hare Intl., returning Tue, Nov 17, priced at $334 found 1 day ago
Sun Country Airlines
Wed, Nov 25 - Sat, Nov 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$413 Roundtrip, found 17 hours ago
$413
Roundtrip
found 17 hours ago
Select Sun Country Airlines flight, departing Wed, Nov 25 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Nov 28, priced at $413 found 17 hours ago
American Airlines
Thu, Sep 10 - Sun, Sep 13
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$437 Roundtrip, found 1 day ago
$437
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Sep 10 from Sky Harbor Intl. to Greater Rockford, returning Sun, Sep 13, priced at $437 found 1 day ago
American Airlines
Fri, Sep 25 - Mon, Sep 28
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$504 Roundtrip, found 4 hours ago
$504
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Fri, Sep 25 from Dallas-Fort Worth Intl. to Greater Rockford, returning Mon, Sep 28, priced at $504 found 4 hours ago
JetBlue Airways
Thu, Nov 12 - Sat, Nov 14
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$547 Roundtrip, found 3 hours ago
$547
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Thu, Nov 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Nov 14, priced at $547 found 3 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 October, 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 15 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 $145, 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 $145 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$63

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! (10,269 reviews)
"Nice"

Reviewed on Sep 4, 2026

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Congress Plaza Hotel
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 ...
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The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (888 reviews)
"We thoroughly enjoyed our stay at Kasa- check in instructions were clear and hassle free. The unit was spacious and clean, with a terrific view. Highly recommended!"

Reviewed on Sep 4, 2026

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Kasa Magnificent Mile Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,399 reviews)
"Room carpets were too old, room is to small may use for solo. good place for down town"

Reviewed on Sep 4, 2026

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River Hotel
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
8/10 Very Good! (1,566 reviews)
"Parking : called ahead to ask about parking our trailer we pulled and was told a garage to use then it was an issue once we got there."

Reviewed on Sep 3, 2026

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Hampton Inn Chicago Downtown/Magnificent Mile
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 ...
8.6/10 Excellent! (3,141 reviews)
"Overall great experience staying here. The view was really nice and the room was spacious and clean. Loved that it was walking distance from the stadium."

Reviewed on Sep 4, 2026

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Hilton Chicago
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! (3,483 reviews)
"Awesome location! The staff were very friendly! The rooms were clean and comfortable."

Reviewed on Sep 4, 2026

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Hyatt Regency Chicago
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
9.6/10 Exceptional! (4,720 reviews)
"c"

Reviewed on Sep 4, 2026

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L7 Chicago by LOTTE
See all 5,381 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 ...
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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 ...
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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! (2,392 reviews)
"Great place to stay. Wonderful staff and clean rooms. Breakfast with many options to accommodate varied preferences."

Reviewed on Sep 3, 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 ...
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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 ...
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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 ...
6/10 (1,002 reviews)
"It’s very Good, good location, good parking, good room and good employees"

Reviewed on Sep 2, 2026

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Carlton Inn Midway
See all 5,381 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.