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Chicago

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Chicago Flights as Low as $121

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

Frontier Airlines
Sat, Aug 29 - Sun, Sep 6
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$121 Roundtrip, found 1 day ago
$121
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, Sep 6, priced at $121 found 1 day ago
Frontier Airlines
Tue, Jun 2 - Sat, Jun 6
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$124 Roundtrip, found 3 days ago
$124
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Jun 2 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Jun 6, priced at $124 found 3 days ago
Spirit Airlines
Tue, Aug 11 - Sat, Aug 22
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$128 Roundtrip, found 5 days ago
$128
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Tue, Aug 11 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Aug 22, priced at $128 found 5 days ago
Frontier Airlines
Tue, Jul 28 - Tue, Aug 11
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$169 Roundtrip, found 20 hours ago
$169
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Tue, Jul 28 from Harry Reid Intl. to O'Hare Intl., returning Tue, Aug 11, priced at $169 found 20 hours ago
Frontier Airlines
Mon, Jun 8 - Fri, Jun 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 4 days ago
$172
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Jun 8 from Los Angeles Intl. to O'Hare Intl., returning Fri, Jun 19, priced at $172 found 4 days ago
Bargain Flight
Tue, Oct 20 - Wed, Oct 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$196 Roundtrip, found 3 days ago
$196
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Tue, Oct 20 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Oct 28, priced at $196 found 3 days ago
American Airlines
Wed, May 27 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$204 Roundtrip, found 19 hours ago
$204
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Wed, May 27 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 3, priced at $204 found 19 hours ago
Delta
Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Aug 12 from Los Angeles Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $217 found 3 days ago
Frontier Airlines
Sat, May 16 - Tue, May 19
LAS
Harry Reid Intl.
MDW
Midway Intl.
$220 Roundtrip, found 6 days ago
$220
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 16 from Harry Reid Intl. to Midway Intl., returning Tue, May 19, priced at $220 found 6 days ago
Delta
Sat, May 23 - Tue, May 26
LAX
Los Angeles Intl.
MDW
Midway Intl.
$249 Roundtrip, found 1 hour ago
$249
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, May 23 from Los Angeles Intl. to Midway Intl., returning Tue, May 26, priced at $249 found 1 hour ago
Delta
Tue, Oct 20 - Wed, Oct 28
DAL
Love Field
ORD
O'Hare Intl.
$265 Roundtrip, found 3 days ago
$265
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Oct 20 from Love Field to O'Hare Intl., returning Wed, Oct 28, priced at $265 found 3 days ago
Delta
Tue, Jun 2 - Wed, Jun 3
DAL
Love Field
MDW
Midway Intl.
$271 Roundtrip, found 3 days ago
$271
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jun 2 from Love Field to Midway Intl., returning Wed, Jun 3, priced at $271 found 3 days ago
Contour Airlines
Mon, May 11 - Fri, May 15
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$286 Roundtrip, found 4 hours ago
$286
Roundtrip
found 4 hours ago
Select Contour Airlines flight, departing Mon, May 11 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Fri, May 15, priced at $286 found 4 hours ago
American Airlines
Thu, May 28 - Mon, Jun 1
LAS
Harry Reid Intl.
RFD
Greater Rockford
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, May 28 from Harry Reid Intl. to Greater Rockford, returning Mon, Jun 1, priced at $314 found 1 day ago
American Airlines
Sun, May 24 - Sun, May 31
LAX
Los Angeles Intl.
RFD
Greater Rockford
$344 Roundtrip, found 1 day ago
$344
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, May 24 from Los Angeles Intl. to Greater Rockford, returning Sun, May 31, priced at $344 found 1 day ago
American Airlines
Sun, May 24 - Tue, May 26
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$389 Roundtrip, found 8 hours ago
$389
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sun, May 24 from Dallas-Fort Worth Intl. to Greater Rockford, returning Tue, May 26, priced at $389 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 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 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 $121, 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 $121 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$74

Last Minute Hotel Deals in Chicago

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! (2,662 reviews)
Staff was wonderful.

Reviewed on May 3, 2026

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Hotel Felix River North/Magnificent Mile
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! (5,154 reviews)
EXCELLENT LOCATION

Reviewed on May 2, 2026

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River 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 ...
8.4/10 Very Good! (2,273 reviews)
Good for an airport hotel. Definitely dated.

Reviewed on May 2, 2026

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Hilton Chicago O'Hare Airport
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! (4,031 reviews)
Breakfast was not good as we expected for 4 star hotel. The hotel was not calm and we had so much noise in our corridor

Reviewed on May 2, 2026

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Hotel Riu Plaza Chicago
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (3,477 reviews)
Staff was great and very helpful.

Reviewed on May 2, 2026

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Club Quarters Hotel, Central Loop, Chicago
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! (4,247 reviews)
I don’t understand the excellent reviews at this hotel. The hotel was in a great location. However the room was very dated and smelled of mildew and mold. Shower was filthy. Furniture was falling apart. Would not stay here again.

Reviewed on May 2, 2026

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Hilton Chicago/Magnificent Mile Suites
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (2,291 reviews)
clean room, wonderful pool, breakfast was very good, everything felt effortless.

Reviewed on Apr 30, 2026

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Holiday Inn Chicago Dwtn - The Mart by IHG
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! (10,133 reviews)
Staff was very helpful. They brought us a portable heater and extra blankets, provide room service, and were in general very helpful. Bed was comfortable. The main floor is lovely. The bar and food were solid. My only complaints were that we could not control the room temperature ourselves and it ...

Reviewed on May 2, 2026

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Congress Plaza Hotel
See all 5,555 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! (1,656 reviews)
Everything was exquisite

Reviewed on May 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 ...
7.4/10 Good! (1,391 reviews)
The hotel was clean and quiet, but the downside was that the beds rolled around to much instead of staying in place, and there was long strands of hair all over the towels, tub, and toilet. Besides all the hair it was a nice room.

Reviewed on May 3, 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! (2,271 reviews)
Airport shuttle such a win

Reviewed on May 2, 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! (1,003 reviews)
Clean, convenient, nice restaurant on the property

Reviewed on May 1, 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 ...
9.6/10 Exceptional! (2,048 reviews)
I decided to stay at this hotel based solely on the pictures and location provided online. The hotel was spotless, and the staff was incredibly polite and friendly. For dinner, I opted for the hotel’s restaurant, “The Ashburn.” The food was decent, but be prepared to pay a premium since it’s a more ...

Reviewed on May 2, 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 (1,001 reviews)
The pictures on the website is a lie. The rooms are alot smaller. Bathroom door didn't fully work. Supposed to be a queen size bed but gave me a full size. Bed was super hard. Staff didn't want to bring extra pillows. Had a 2 night stay but left after first night.

Reviewed on Apr 19, 2026

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Carlton Inn Midway
See all 5,555 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.