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Chicago

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Chicago Flights as Low as $58

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

Frontier Airlines
Tue, May 12 - Wed, May 13
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$58 Roundtrip, found 17 hours ago
$58
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Tue, May 12 from George Bush Intercontinental to O'Hare Intl., returning Wed, May 13, priced at $58 found 17 hours ago
Frontier Airlines
Tue, May 12 - Wed, May 13
DEN
Denver Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 12 from Denver Intl. to O'Hare Intl., returning Wed, May 13, priced at $58 found 1 day ago
Frontier Airlines
Fri, Jul 3 - Sat, Jul 4
MCO
Orlando Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 17 hours ago
$88
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Fri, Jul 3 from Orlando Intl. to O'Hare Intl., returning Sat, Jul 4, priced at $88 found 17 hours ago
Spirit Airlines
Tue, May 12 - Tue, May 12
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$89 Roundtrip, found 1 day ago
$89
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, May 12 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 12, priced at $89 found 1 day ago
Frontier Airlines
Sat, May 9 - Tue, May 12
MCO
Orlando Intl.
MDW
Midway Intl.
$160 Roundtrip, found 4 days ago
$160
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, May 9 from Orlando Intl. to Midway Intl., returning Tue, May 12, priced at $160 found 4 days ago
United
Tue, May 12 - Tue, May 19
DEN
Denver Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select United flight, departing Tue, May 12 from Denver Intl. to O'Hare Intl., returning Tue, May 19, priced at $163 found 1 day ago
American Airlines
Tue, May 12 - Tue, May 19
DEN
Denver Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, May 12 from Denver Intl. to O'Hare Intl., returning Tue, May 19, priced at $163 found 1 day ago
Frontier Airlines
Thu, May 28 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$168 Roundtrip, found 3 days ago
$168
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, May 28 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 3, priced at $168 found 3 days ago
Frontier Airlines
Wed, May 6 - Tue, May 12
DEN
Denver Intl.
MDW
Midway Intl.
$186 Roundtrip, found 3 days ago
$186
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, May 6 from Denver Intl. to Midway Intl., returning Tue, May 12, priced at $186 found 3 days ago
Frontier Airlines
Mon, May 11 - Tue, May 12
IAH
George Bush Intercontinental
MDW
Midway Intl.
$191 Roundtrip, found 5 days ago
$191
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, May 11 from George Bush Intercontinental to Midway Intl., returning Tue, May 12, priced at $191 found 5 days ago
Delta
Wed, Jul 1 - Wed, Jul 1
MCO
Orlando Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 14 hours ago
$197
Roundtrip
found 14 hours ago
Select Delta flight, departing Wed, Jul 1 from Orlando Intl. to O'Hare Intl., returning Wed, Jul 1, priced at $197 found 14 hours ago
American Airlines
Wed, May 27 - Thu, May 28
MCO
Orlando Intl.
RFD
Greater Rockford
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to Greater Rockford, returning Thu, May 28, priced at $219 found 1 day ago
Frontier Airlines
Tue, May 19 - Thu, May 28
LAX
Los Angeles Intl.
MDW
Midway Intl.
$236 Roundtrip, found 1 day ago
$236
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 $236 found 1 day ago
American Airlines
Fri, May 29 - Sat, Aug 1
IAH
George Bush Intercontinental
RFD
Greater Rockford
$281 Roundtrip, found 3 days ago
$281
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, May 29 from George Bush Intercontinental to Greater Rockford, returning Sat, Aug 1, priced at $281 found 3 days ago
American Airlines
Fri, May 1 - Tue, May 5
DEN
Denver Intl.
RFD
Greater Rockford
$360 Roundtrip, found 19 hours ago
$360
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Fri, May 1 from Denver Intl. to Greater Rockford, returning Tue, May 5, priced at $360 found 19 hours ago
American Airlines
Mon, May 25 - Tue, May 26
LAX
Los Angeles Intl.
RFD
Greater Rockford
$375 Roundtrip, found 2 days ago
$375
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, May 25 from Los Angeles Intl. to Greater Rockford, returning Tue, May 26, priced at $375 found 2 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 May, 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 $58, 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 $58 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
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! (10,133 reviews)
wifi wouldn’t connect, when we called the front desk to ask (I had work I needed to do, and specifically checked before booking that the room included wifi) was met with attitude to “just connect” even though the wifi network wasn’t visible or available. also, you have no control over the temperature ...

Reviewed on Apr 24, 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! (2,636 reviews)
The staff were extremely impressed and helpful. Help me with restaurant choices, where to go for tours. Only thing I regretted was not packing the proper clothes for the chance of weather. It was my personal birthday present to me and I did enjoyed myself.

Reviewed on Apr 24, 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! (5,125 reviews)
Wonderful and helpful sstaff. Excellent location

Reviewed on Apr 24, 2026

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River Hotel
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! (3,456 reviews)
AC was broken, phone was broken, room was run down

Reviewed on Apr 24, 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! (4,189 reviews)
good

Reviewed on Apr 23, 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! (3,951 reviews)
Awesome stay, loved the minimalist decor and fabulously breakfast buffet.

Reviewed on Apr 25, 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! (5,891 reviews)
No complaints at this property. Always stay here when I’m in Chicago. Great experience and in the center of everything

Reviewed on Apr 25, 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! (1,127 reviews)
Great staff and clean facilities

Reviewed on Apr 25, 2026

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The Westin Michigan Avenue Chicago
See all 5,597 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! (1,648 reviews)
Appreciate the courtesy wake-up call.

Reviewed on Apr 24, 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! (1,367 reviews)
Everything was excellent

Reviewed on Apr 21, 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! (2,262 reviews)
Breakfast is good, room was super clean. Overall a great place

Reviewed on Apr 24, 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! (1,002 reviews)
Cheerful and accommodating staff.

Reviewed on Apr 22, 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! (2,035 reviews)
Beautiful hotel. Comfy beds, plenty of towels. Near airport but didn't hear the planes flying over us at all. Starbucks inside hotel also plenty of nice restaurants on the property. The staff was very friendly. I will definitely stay everytime I am I'm Rosemont.

Reviewed on Apr 21, 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 (1,003 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 5,597 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.