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Chicago

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Chicago Flights as Low as $115

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

Frontier Airlines
Tue, Jul 7 - Tue, Jul 14
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$115 Roundtrip, found 13 hours ago
$115
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Jul 7 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Tue, Jul 14, priced at $115 found 13 hours ago
Delta
Wed, Jul 1 - Wed, Jul 22
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jul 1 from Minneapolis - St. Paul Intl. to Midway Intl., returning Wed, Jul 22, priced at $137 found 2 days ago
Delta
Tue, Jul 21 - Wed, Jul 22
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 7 hours ago
$137
Roundtrip
found 7 hours ago
Select Delta flight, departing Tue, Jul 21 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Wed, Jul 22, priced at $137 found 7 hours ago
United
Wed, Jul 29 - Tue, Aug 18
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select United flight, departing Wed, Jul 29 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Tue, Aug 18, priced at $137 found 5 days ago
American Airlines
Wed, Jul 29 - Tue, Aug 18
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Jul 29 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Tue, Aug 18, priced at $137 found 5 days ago
Frontier Airlines
Sat, Jun 20 - Wed, Jul 1
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 6 hours ago
$152
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Jun 20 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 1, priced at $152 found 6 hours ago
Frontier Airlines
Tue, Jul 28 - Thu, Jul 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$166 Roundtrip, found 3 hours ago
$166
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, Jul 28 from Los Angeles Intl. to O'Hare Intl., returning Thu, Jul 30, priced at $166 found 3 hours ago
Frontier Airlines
Tue, Oct 13 - Sat, Oct 17
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$172 Roundtrip, found 3 days ago
$172
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Oct 13 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Oct 17, priced at $172 found 3 days ago
Sun Country Airlines
Fri, Jul 24 - Sat, Jul 25
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$187 Roundtrip, found 7 hours ago
$187
Roundtrip
found 7 hours ago
Select Sun Country Airlines flight, departing Fri, Jul 24 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Sat, Jul 25, priced at $187 found 7 hours ago
JetBlue Airways
Wed, Sep 9 - Tue, Sep 15
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 9 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Tue, Sep 15, priced at $189 found 1 day ago
Delta
Tue, Sep 1 - Tue, Sep 8
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 1 from Fort Lauderdale - Hollywood Intl. to Midway Intl., returning Tue, Sep 8, priced at $217 found 2 days ago
Delta
Wed, Jul 22 - Wed, Jul 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$239 Roundtrip, found 3 days ago
$239
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jul 22 from Los Angeles Intl. to Midway Intl., returning Wed, Jul 29, priced at $239 found 3 days ago
Delta
Tue, Jul 21 - Wed, Jul 29
DAL
Love Field
MDW
Midway Intl.
$301 Roundtrip, found 2 days ago
$301
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jul 21 from Love Field to Midway Intl., returning Wed, Jul 29, priced at $301 found 2 days ago
Delta
Wed, Sep 9 - Tue, Sep 15
DAL
Love Field
ORD
O'Hare Intl.
$301 Roundtrip, found 1 day ago
$301
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 15, priced at $301 found 1 day ago
American Airlines
Thu, Jan 21 - Tue, Jan 26
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$307 Roundtrip, found 1 day ago
$307
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jan 21 from Dallas-Fort Worth Intl. to Greater Rockford, returning Tue, Jan 26, priced at $307 found 1 day ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$418 Roundtrip, found 3 days ago
$418
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $418 found 3 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 July, 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 $115, 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 $115 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$99

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! (10,131 reviews)
"Did not have hot water when we returned to room after concert. Next morning called and maintenance came to fix. Good location to walk to South Shore train station and Grant Park"

Reviewed on May 23, 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! (4,214 reviews)
"One of the best hotels I’ve stayed in!"

Reviewed on May 23, 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! (2,715 reviews)
"A decent buisness class hotel. No frills. Rooms are smaller, the queen beds are not true queens, and much smaller."

Reviewed on May 22, 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 ...
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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! (5,190 reviews)
"The staff was very helpful and friendly."

Reviewed on May 22, 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! (2,324 reviews)
"The location is very good, but the hotel needs to make some improvements. First, when you enter, there is a strong smell of humidity, which I imagine is coming from the carpet. The same smell was noticeable in the hallways and in the room. In the room, I found that the sink was clogged, and the shower ..."

Reviewed on May 21, 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! (2,164 reviews)
"Amazing staff. Clean rooms!"

Reviewed on May 21, 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! (3,016 reviews)
"The staff was lovely as always. The room was nice and clean."

Reviewed on May 22, 2026

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Freehand Chicago
See all 5,558 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! (1,672 reviews)
"Unhelpful They asked me to pay for an early check in evennthough i have paid my stay. I missed my one night due to delayed flights. Staff were very unhelpful. Not a good stay"

Reviewed on May 23, 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! (1,432 reviews)
"The staff were very helpful and kind. But hotel and our room was not clean. Hotel definitely needs some serious renovation ."

Reviewed on May 23, 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! (2,300 reviews)
"Dust on counter. Door to bathroom didn't latch. The shower head would run even when it wasn't supposed to. The AC was pretty loud. Very little soundproofing."

Reviewed on May 23, 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)
"Staff is nice. Hotel needs a little upgrade. Breakfast was amazing!!"

Reviewed on May 20, 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! (2,071 reviews)
"Pretty good!"

Reviewed on May 23, 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)
"No hot water Disgusting room cleanliness"

Reviewed on May 22, 2026

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Carlton Inn Midway
See all 5,558 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.