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Chicago

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Chicago Flights as Low as $98

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

Frontier Airlines
Tue, Sep 29 - Tue, Oct 6
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Sep 29 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Oct 6, priced at $98 found 2 days ago
Frontier Airlines
Sat, Aug 15 - Thu, Sep 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Aug 15 from Los Angeles Intl. to O'Hare Intl., returning Thu, Sep 3, priced at $152 found 3 days ago
United
Wed, Jul 1 - Tue, Aug 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 11 hours ago
$153
Roundtrip
found 11 hours ago
Select United flight, departing Wed, Jul 1 from Logan Intl. to O'Hare Intl., returning Tue, Aug 4, priced at $153 found 11 hours ago
JetBlue Airways
Wed, Aug 26 - Tue, Sep 15
BOS
Logan Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, Aug 26 from Logan Intl. to O'Hare Intl., returning Tue, Sep 15, priced at $157 found 5 days ago
Frontier Airlines
Tue, Jul 7 - Wed, Jul 8
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$162 Roundtrip, found 6 days ago
$162
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Jul 7 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Jul 8, priced at $162 found 6 days ago
Delta
Tue, Aug 4 - Thu, Aug 13
BOS
Logan Intl.
ORD
O'Hare Intl.
$179 Roundtrip, found 4 days ago
$179
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Aug 4 from Logan Intl. to O'Hare Intl., returning Thu, Aug 13, priced at $179 found 4 days ago
American Airlines
Wed, Jul 1 - Wed, Aug 5
BOS
Logan Intl.
RFD
Greater Rockford
$191 Roundtrip, found 6 hours ago
$191
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Jul 1 from Logan Intl. to Greater Rockford, returning Wed, Aug 5, priced at $191 found 6 hours ago
Delta
Tue, Jul 21 - Tue, Jul 28
LAX
Los Angeles Intl.
MDW
Midway Intl.
$265 Roundtrip, found 6 days ago
$265
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jul 21 from Los Angeles Intl. to Midway Intl., returning Tue, Jul 28, priced at $265 found 6 days ago
Alaska Airlines
Tue, Oct 13 - Sat, Oct 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$291 Roundtrip, found 1 day ago
$291
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Oct 13 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 17, priced at $291 found 1 day ago
Delta
Wed, Sep 16 - Sat, Sep 19
DAL
Love Field
ORD
O'Hare Intl.
$292 Roundtrip, found 6 days ago
$292
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Sep 16 from Love Field to O'Hare Intl., returning Sat, Sep 19, priced at $292 found 6 days 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
Frontier Airlines
Fri, Jul 3 - Mon, Jul 6
BOS
Logan Intl.
MDW
Midway Intl.
$310 Roundtrip, found 1 day ago
$310
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jul 3 from Logan Intl. to Midway Intl., returning Mon, Jul 6, priced at $310 found 1 day ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$332 Roundtrip, found 6 days ago
$332
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $332 found 6 days ago
Contour Airlines
Mon, Sep 28 - Wed, Sep 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$334 Roundtrip, found 1 day ago
$334
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Mon, Sep 28 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Sep 30, priced at $334 found 1 day ago
Delta
Sat, Jun 20 - Tue, Jul 7
DAL
Love Field
MDW
Midway Intl.
$389 Roundtrip, found 23 hours ago
$389
Roundtrip
found 23 hours ago
Select Delta flight, departing Sat, Jun 20 from Love Field to Midway Intl., returning Tue, Jul 7, priced at $389 found 23 hours ago
Sun Country Airlines
Fri, Sep 4 - Sun, Sep 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$498 Roundtrip, found 17 hours ago
$498
Roundtrip
found 17 hours ago
Select Sun Country Airlines flight, departing Fri, Sep 4 from Los Angeles Intl. to O'Hare Intl., returning Sun, Sep 6, priced at $498 found 17 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 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 $98, 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 $98 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$131

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! (10,179 reviews)
"Location was good to train station and grand park but biggest issue we had is no water pressure and it was at best lukewarm. This makes me now want to always check first before booking anything how their water service is. It was terrible and when I checked previous reviews it was one of biggest complaints. ..."

Reviewed on Jun 6, 2026

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Congress Plaza Hotel
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! (1,524 reviews)
"Great location, lovely hotel with a roof top bar and cheerful staff."

Reviewed on Jun 6, 2026

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The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,620 reviews)
"Very helpful, polite and nice staff. Clean and confortable rooms. Close to airport."

Reviewed on Jun 5, 2026

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Hyatt Regency O'Hare Chicago
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! (4,358 reviews)
"Excelente atención de todo el personal del hotel. Muy limpio todo, un desayuno super bueno y muy variado. El rooftop con excelente servicio y ofertas, además de vistas increíbles. Excelente ubicación. Definitivamente la cadena hotelera Riu se ha convertido en mi favorita para cualquier destino🤗"

Reviewed on Jun 5, 2026

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Hotel Riu Plaza Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,551 reviews)
"Everything was good, great location. We walked everywhere, room was clean."

Reviewed on Jun 6, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
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! (2,476 reviews)
"Check in was horrible. The longest lines you can imagine….face me 250 Hilton points….not useful for me. Property is beautiful if you look closely but it is not well maintained."

Reviewed on Jun 4, 2026

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Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
9/10 Wonderful! (2,239 reviews)
"I had an amazing time in Chicago, not one complaint. Everyone was pleasant and my room was clean."

Reviewed on Jun 4, 2026

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Crowne Plaza Chicago West Loop by IHG
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! (3,064 reviews)
"It was a really neat hotel. I liked the style. Wasn't sure why we had to make our own beds though. Also, the phone didn't work in the room, so I tried to call the front desk from my phone. They immediately put me on hold "for a minute", which turned into 5. I hung up to call back thinking they forgot ..."

Reviewed on Jun 6, 2026

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Freehand Chicago
See all 5,527 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! (1,699 reviews)
"The breakfast wasn’t very good"

Reviewed on Jun 5, 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! (1,483 reviews)
"My stay was great. I had a wonderful time. The staff was very friendly and helpful throughout my stay. The free breakfast was really good and had a nice selection. I only have one small complaint, my room was a little bit dirty. I also bring my own cleaning supplies so that wasn't a major concern ..."

Reviewed on Jun 6, 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! (2,327 reviews)
"Great room and breakfast, staff were very attentive too."

Reviewed on Jun 4, 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! (1,010 reviews)
"Staff was wonderful, Bar Louie food was terrible."

Reviewed on Jun 6, 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! (2,076 reviews)
"The room was so clean and staff was very nice. The parking was a little bit pricey per day but overall would recommend again definitely!"

Reviewed on Jun 5, 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 (1,008 reviews)
"The stay was disappointing from the moment we arrived. The pictures online were misleading, and the actual room looked nothing like what was advertised. There was no privacy at all — the room had only thin blinds with no curtains, and anyone outside could easily see in. The layout felt unsafe, more ..."

Reviewed on Jun 6, 2026

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Carlton Inn Midway
See all 5,527 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.