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Chicago

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Chicago Flights as Low as $76

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

Frontier Airlines
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, found 1 hour ago
$76
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $76 found 1 hour ago
Frontier Airlines
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$78 Roundtrip, found 18 hours ago
$78
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, May 13, priced at $78 found 18 hours ago
Spirit Airlines
Mon, Jun 22 - Sat, Jul 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$114 Roundtrip, found 21 hours ago
$114
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Mon, Jun 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Jul 4, priced at $114 found 21 hours ago
Frontier Airlines
Wed, May 13 - Wed, May 27
BOS
Logan Intl.
ORD
O'Hare Intl.
$154 Roundtrip, found 21 hours ago
$154
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Wed, May 13 from Logan Intl. to O'Hare Intl., returning Wed, May 27, priced at $154 found 21 hours ago
Frontier Airlines
Fri, May 29 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$159 Roundtrip, found 8 hours ago
$159
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Fri, May 29 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 3, priced at $159 found 8 hours ago
Frontier Airlines
Wed, May 6 - Tue, May 12
BOS
Logan Intl.
MDW
Midway Intl.
$164 Roundtrip, found 16 hours ago
$164
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Wed, May 6 from Logan Intl. to Midway Intl., returning Tue, May 12, priced at $164 found 16 hours ago
Delta
Mon, Jun 1 - Thu, Jun 11
DAL
Love Field
MDW
Midway Intl.
$167 Roundtrip, found 5 days ago
$167
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Jun 1 from Love Field to Midway Intl., returning Thu, Jun 11, priced at $167 found 5 days ago
United
Wed, Jul 1 - Tue, Aug 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 1 hour ago
$167
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Jul 1 from Logan Intl. to O'Hare Intl., returning Tue, Aug 4, priced at $167 found 1 hour ago
JetBlue Airways
Wed, Jul 1 - Tue, Aug 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 1 hour ago
$167
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Wed, Jul 1 from Logan Intl. to O'Hare Intl., returning Tue, Aug 4, priced at $167 found 1 hour ago
American Airlines
Wed, Jul 1 - Tue, Aug 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 1 hour ago
$167
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Jul 1 from Logan Intl. to O'Hare Intl., returning Tue, Aug 4, priced at $167 found 1 hour ago
American Airlines
Wed, Jul 1 - Wed, Aug 5
BOS
Logan Intl.
RFD
Greater Rockford
$195 Roundtrip, found 4 days ago
$195
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 1 from Logan Intl. to Greater Rockford, returning Wed, Aug 5, priced at $195 found 4 days ago
Frontier Airlines
Tue, May 19 - Thu, May 28
LAX
Los Angeles Intl.
MDW
Midway Intl.
$246 Roundtrip, found 1 day ago
$246
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 19 from Los Angeles Intl. to Midway Intl., returning Thu, May 28, priced at $246 found 1 day ago
Delta
Tue, May 12 - Sat, May 16
DAL
Love Field
ORD
O'Hare Intl.
$255 Roundtrip, found 1 hour ago
$255
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, May 12 from Love Field to O'Hare Intl., returning Sat, May 16, priced at $255 found 1 hour ago
American Airlines
Mon, May 25 - Tue, May 26
LAX
Los Angeles Intl.
RFD
Greater Rockford
$315 Roundtrip, found 5 days ago
$315
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, May 25 from Los Angeles Intl. to Greater Rockford, returning Tue, May 26, priced at $315 found 5 days ago
American Airlines
Thu, May 14 - Mon, May 18
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$323 Roundtrip, found 6 hours ago
$323
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Thu, May 14 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Mon, May 18, priced at $323 found 6 hours ago
Alaska Airlines
Tue, May 12 - Wed, May 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$386 Roundtrip, found 20 hours ago
$386
Roundtrip
found 20 hours ago
Select Alaska Airlines flight, departing Tue, May 12 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 13, priced at $386 found 20 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 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 $76, 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 $76 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$76

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! (10,159 reviews)
Hotel has the markings of being grand, but needs a renovation in a lot of areas. The biggest issue we had is that the a/c is not adjustable in each room and the building was very warm on the 75 degree day in April. We called the front desk and they did bring us a fan that helped some and we realized ...

Reviewed on Apr 20, 2026

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Congress Plaza Hotel
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! (2,633 reviews)
Great place to stay! Restaurants and bars are within walking distance and everything else is a 20-30 minute walk. Staff was very friendly and helpful.

Reviewed on Apr 21, 2026

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Hotel Felix River North/Magnificent Mile
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! (3,444 reviews)
Hotel is a little dated but clean and tidy, excellent location for public transport and walk to the lake. We didnt eat here so can not comment. Central down town in the Loop so expect some road news.

Reviewed on Apr 20, 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! (4,178 reviews)
Bien situé

Reviewed on Apr 21, 2026

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Hilton Chicago/Magnificent Mile Suites
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! (3,908 reviews)
Excellent, customer service. Excellent, customer service excellent room excellent breakfast excellent rooftop excellent lounging area top-tier hotel.

Reviewed on Apr 20, 2026

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Hotel Riu Plaza Chicago
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! (5,878 reviews)
Very Good breakfast

Reviewed on Apr 20, 2026

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Embassy Suites by Hilton Chicago Downtown River North
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
909 North Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
8.8/10 Excellent! (1,129 reviews)
Location was great. Walking distance to everything

Reviewed on Apr 21, 2026

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The Westin Michigan Avenue Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,403 reviews)
We love the Palmer House! This is our “go to” hotel when we travel to Chicago. It is close to theaters, concert halls, Michigan Ave with museums, restaurants, parks, etc. The hotel lobby is incredible! A great place to relax, have a beverage, people watch, and enjoy. The room we recently stayed in ...

Reviewed on Apr 20, 2026

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Palmer House a Hilton Hotel
See all 5,603 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! (1,646 reviews)
Easy parking, courteous, check-in, room was clean with a good mattress. Complementary breakfast was below expectations, juice machine was broken, coffee was weak, small space with plenty of coughing patrons

Reviewed on Apr 20, 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! (1,375 reviews)
Special mention for Ramad who was exceptional We had a delayed flight and arrived later than our initial arrival time He was kind and professional and assisted us with our two young children

Reviewed on Apr 20, 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! (2,268 reviews)
Breakfast was great. Our first keycard didn't work. We had to get replacement. The bed was very comfortable

Reviewed on Apr 20, 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! (1,005 reviews)
Room was clean, bed was comfortable, Check in/out was easy and having Bar Louie on property made food and entertainment easy. Will definitely stay here again.

Reviewed on Apr 16, 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! (2,037 reviews)
Very nice

Reviewed on Apr 20, 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 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 5,603 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.