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Chicago

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Chicago Flights as Low as $66

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

Frontier Airlines
Wed, Sep 23 - Tue, Sep 29
MCO
Orlando Intl.
ORD
O'Hare Intl.
$66 Roundtrip, found 2 days ago
$66
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Sep 23 from Orlando Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $66 found 2 days ago
Frontier Airlines
Mon, Jul 13 - Tue, Jul 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$162 Roundtrip, found 3 days ago
$162
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Jul 13 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Jul 28, priced at $162 found 3 days ago
United
Wed, Aug 19 - Tue, Sep 8
MCO
Orlando Intl.
ORD
O'Hare Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select United flight, departing Wed, Aug 19 from Orlando Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $169 found 2 days ago
American Airlines
Wed, Aug 19 - Tue, Sep 8
MCO
Orlando Intl.
ORD
O'Hare Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Aug 19 from Orlando Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $169 found 2 days ago
Frontier Airlines
Sun, Aug 2 - Sat, Aug 15
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Aug 2 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Aug 15, priced at $189 found 1 day ago
Frontier Airlines
Tue, Jun 9 - Wed, Jun 17
MCO
Orlando Intl.
MDW
Midway Intl.
$198 Roundtrip, found 3 days ago
$198
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Orlando Intl. to Midway Intl., returning Wed, Jun 17, priced at $198 found 3 days ago
American Airlines
Wed, May 27 - Thu, May 28
MCO
Orlando Intl.
RFD
Greater Rockford
$222 Roundtrip, found 7 hours ago
$222
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to Greater Rockford, returning Thu, May 28, priced at $222 found 7 hours ago
Bargain Flight
Wed, Aug 12 - Mon, Aug 17
SEA
Seattle - Tacoma Intl.
ORD
O'Hare Intl.
$264 Roundtrip, found 3 hours ago
$264
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Wed, Aug 12 from Seattle - Tacoma Intl. to O'Hare Intl., returning Mon, Aug 17, priced at $264 found 3 hours ago
Delta
Sat, Jul 18 - Tue, Jul 28
DAL
Love Field
ORD
O'Hare Intl.
$301 Roundtrip, found 1 day ago
$301
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jul 18 from Love Field to O'Hare Intl., returning Tue, Jul 28, priced at $301 found 1 day ago
Delta
Sat, Jul 25 - Sat, Aug 8
DAL
Love Field
MDW
Midway Intl.
$355 Roundtrip, found 4 days ago
$355
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Jul 25 from Love Field to Midway Intl., returning Sat, Aug 8, priced at $355 found 4 days ago
American Airlines
Sun, May 24 - Tue, May 26
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$371 Roundtrip, found 3 days ago
$371
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, May 24 from Dallas-Fort Worth Intl. to Greater Rockford, returning Tue, May 26, priced at $371 found 3 days ago
Alaska Airlines
Thu, Aug 27 - Sun, Sep 20
PAE
Seattle Paine Field Intl. Airport
ORD
O'Hare Intl.
$375 Roundtrip, found 13 hours ago
$375
Roundtrip
found 13 hours ago
Select Alaska Airlines flight, departing Thu, Aug 27 from Seattle Paine Field Intl. Airport to O'Hare Intl., returning Sun, Sep 20, priced at $375 found 13 hours ago
American Airlines
Sat, May 23 - Mon, Jun 1
SEA
Seattle - Tacoma Intl.
RFD
Greater Rockford
$446 Roundtrip, found 3 days ago
$446
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, May 23 from Seattle - Tacoma Intl. to Greater Rockford, returning Mon, Jun 1, priced at $446 found 3 days ago
American Airlines
Mon, Jun 1 - Tue, Jun 2
YOW
Macdonald-Cartier Intl.
ORD
O'Hare Intl.
$448 Roundtrip, found 10 hours ago
$448
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Mon, Jun 1 from Macdonald-Cartier Intl. to O'Hare Intl., returning Tue, Jun 2, priced at $448 found 10 hours ago
Delta
Sat, May 23 - Tue, Jun 2
SEA
Seattle - Tacoma Intl.
MDW
Midway Intl.
$537 Roundtrip, found 14 hours ago
$537
Roundtrip
found 14 hours ago
Select Delta flight, departing Sat, May 23 from Seattle - Tacoma Intl. to Midway Intl., returning Tue, Jun 2, priced at $537 found 14 hours ago
Porter Airlines
Mon, Jun 1 - Thu, Jun 4
YOW
Macdonald-Cartier Intl.
MDW
Midway Intl.
$546 Roundtrip, found 10 hours ago
$546
Roundtrip
found 10 hours ago
Select Porter Airlines flight, departing Mon, Jun 1 from Macdonald-Cartier Intl. to Midway Intl., returning Thu, Jun 4, priced at $546 found 10 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 September, 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 $66, 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 $66 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$70

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! (10,138 reviews)
The bar was very welcoming and the historic ambience and location was exceptional

Reviewed on May 16, 2026

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Congress Plaza Hotel
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! (4,166 reviews)
Bien ubicado, buena relatprecio-calidad y excelente servicio

Reviewed on May 17, 2026

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Hotel Riu Plaza 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! (2,702 reviews)
Amazing place

Reviewed on May 16, 2026

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Hotel Felix River North/Magnificent Mile
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! (1,420 reviews)
Rooms need a renovation.

Reviewed on May 16, 2026

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The Chicago Hotel Collection - 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! (5,184 reviews)
Good for business not really a vacation spot for me. No breakfast and small personal room

Reviewed on May 16, 2026

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River Hotel
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! (2,315 reviews)
Very close to everything

Reviewed on May 16, 2026

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Holiday Inn Chicago Dwtn - The Mart by IHG
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (2,156 reviews)
Very nice, wish there was a pool area Great location Very nice staff

Reviewed on May 17, 2026

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Fairmont Chicago at Millennium Park
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (3,002 reviews)
CONS: stayed in room 808. super dark, only had low lighting, which my partner and i suspect was so they could hide the stains of the room. view was of the ugly back side of the building. worst part was the ac/heater. it was cold when we were there in early may and we were told the heater wasn't working ...

Reviewed on May 17, 2026

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Freehand Chicago
See all 5,549 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! (1,666 reviews)
Building needs upgraded. Stains on Carpet in hallway. Big dents and scratches on all the furniture. Soundprooffing the rooms would be a major improvement. We could here the next rooms entire conversation.

Reviewed on May 16, 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! (1,429 reviews)
This is the 5th year I have stayed here for a local event. There were a couple hiccups this year, but nothing major. Loud people is hallways late at night, tv remote not working, and some confusion over housekeeping. But matters were addressed and taken care of quickly and I will be back next year! ...

Reviewed on May 16, 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! (2,290 reviews)
Everything was great including the breakfast and the free shuttle. Staff even gave us free bottled water when we checked in which was so wonderful since we flew in, didn't have a car and differences in local drinking water often upsets my digestion. Just what we needed after a long international ...

Reviewed on May 14, 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! (1,004 reviews)
NA

Reviewed on May 14, 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! (2,061 reviews)
Room service was nice and friendly. They made a mistake on my meal and corrected it fast and with a smile. I was very happy with service

Reviewed on May 15, 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)
It nice quietly by all store

Reviewed on May 12, 2026

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Carlton Inn Midway
See all 5,549 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.