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Chicago

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Chicago Flights as Low as $83

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.
$83 Roundtrip, found 21 hours ago
$83
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Tue, Sep 29 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Oct 6, priced at $83 found 21 hours ago
Frontier Airlines
Mon, Aug 31 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Aug 31 from Los Angeles Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $120 found 1 day ago
Delta
Tue, Oct 6 - Wed, Oct 14
BOS
Logan Intl.
ORD
O'Hare Intl.
$141 Roundtrip, found 3 days ago
$141
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Oct 6 from Logan Intl. to O'Hare Intl., returning Wed, Oct 14, priced at $141 found 3 days ago
United
Tue, Aug 4 - Tue, Aug 11
BOS
Logan Intl.
ORD
O'Hare Intl.
$145 Roundtrip, found 3 days ago
$145
Roundtrip
found 3 days ago
Select United flight, departing Tue, Aug 4 from Logan Intl. to O'Hare Intl., returning Tue, Aug 11, priced at $145 found 3 days ago
JetBlue Airways
Tue, Aug 4 - Wed, Aug 5
BOS
Logan Intl.
ORD
O'Hare Intl.
$145 Roundtrip, found 2 days ago
$145
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Logan Intl. to O'Hare Intl., returning Wed, Aug 5, priced at $145 found 2 days ago
American Airlines
Tue, Aug 4 - Sat, Aug 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 2 days ago
$153
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Aug 4 from Logan Intl. to O'Hare Intl., returning Sat, Aug 8, priced at $153 found 2 days ago
American Airlines
Tue, Jun 30 - Tue, Aug 4
BOS
Logan Intl.
RFD
Greater Rockford
$173 Roundtrip, just found
$173
Roundtrip
just found
Select American Airlines flight, departing Tue, Jun 30 from Logan Intl. to Greater Rockford, returning Tue, Aug 4, priced at $173 just found
Frontier Airlines
Sat, Sep 12 - Mon, Sep 14
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$186 Roundtrip, found 1 day ago
$186
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Sep 12 from Dallas-Fort Worth Intl. to Midway Intl., returning Mon, Sep 14, priced at $186 found 1 day ago
Delta
Wed, Aug 26 - Wed, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$199 Roundtrip, found 2 days ago
$199
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Aug 26 from Love Field to O'Hare Intl., returning Wed, Sep 9, priced at $199 found 2 days ago
Delta
Tue, Oct 13 - Wed, Oct 21
LAX
Los Angeles Intl.
MDW
Midway Intl.
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Oct 13 from Los Angeles Intl. to Midway Intl., returning Wed, Oct 21, priced at $217 found 2 days ago
Delta
Tue, Oct 13 - Sat, Oct 17
DAL
Love Field
MDW
Midway Intl.
$311 Roundtrip, found 1 day ago
$311
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 13 from Love Field to Midway Intl., returning Sat, Oct 17, priced at $311 found 1 day ago
Alaska Airlines
Wed, Jul 15 - Tue, Jul 28
PDX
Portland Intl.
ORD
O'Hare Intl.
$315 Roundtrip, found 5 days ago
$315
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Jul 15 from Portland Intl. to O'Hare Intl., returning Tue, Jul 28, priced at $315 found 5 days ago
American Airlines
Thu, Jan 21 - Tue, Jan 26
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$329 Roundtrip, found 1 day ago
$329
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 $329 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
American Airlines
Sun, Jul 19 - Tue, Jul 21
PDX
Portland Intl.
RFD
Greater Rockford
$394 Roundtrip, found 8 hours ago
$394
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sun, Jul 19 from Portland Intl. to Greater Rockford, returning Tue, Jul 21, priced at $394 found 8 hours ago
Delta
Sun, Jul 19 - Tue, Jul 21
PDX
Portland Intl.
MDW
Midway Intl.
$467 Roundtrip, found 1 day ago
$467
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Jul 19 from Portland Intl. to Midway Intl., returning Tue, Jul 21, priced at $467 found 1 day 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 $83, 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 $83 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$100

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! (10,264 reviews)
"Great stay!"

Reviewed on Jun 14, 2026

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Congress Plaza Hotel
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! (2,666 reviews)
"Overall stay was great with my brother. I will come back agin. Staff were helpful especially with our shuttle ride to the airport."

Reviewed on Jun 13, 2026

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Hyatt Regency O'Hare Chicago
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! (1,577 reviews)
"My family and I visited on a very busy weekend. I was displeased initially, that the front desk receptionist was by herself considering the hotel was sold out. However, she handled the check-ins with ease; but because of them being short staffed, the extra towels we needed did not get delivered to ..."

Reviewed on Jun 14, 2026

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The Chicago Hotel Collection - Magnificent Mile
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,341 reviews)
"Welcoming, helpful staff, Clean, quiet room, Lovely, comfortable Hilton bed. Outstanding fitness room with new Life Fitness equipment! Great breakfast and Honors benefits, Just steps to terminal and train service."

Reviewed on Jun 13, 2026

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Hilton Chicago O'Hare Airport
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! (1,602 reviews)
"This review reflects both the hotel and Expedia’s handling of the booking. The good: The location is excellent and very accessible. The common areas, including the lobby and bar, are pleasant and well maintained. The bad: The hotel is showing its age. The AC struggled to keep the room comfortable ..."

Reviewed on Jun 13, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
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! (4,420 reviews)
"The entire staff was amazing!"

Reviewed on Jun 13, 2026

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Hilton Chicago/Magnificent Mile Suites
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! (2,788 reviews)
"the only issue i had it was that they didn’t do room service in the room, no new towels , no toilet paper and stuff like that"

Reviewed on Jun 12, 2026

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Hotel Felix River North/Magnificent Mile
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our ...
9.2/10 Wonderful! (3,100 reviews)
"When we arrived our room was dirty. There were used wine glasses, hair beads and rubber bands, and used water bottles. We called and the staff rectified immediately by moving us rooms. Valet was great and so was Micheal Jordan’s Steakhouse. Our bathroom shower had black mold and the vanity was broken ..."

Reviewed on Jun 14, 2026

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InterContinental Chicago Magnificent Mile by IHG
See all 5,512 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! (1,729 reviews)
"Every staff member I encountered was wonderful, shuttle service was very convenient."

Reviewed on Jun 13, 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! (1,504 reviews)
"I enjoyed my stay in a clean room with friendly helpful staff! The breakfast is amazing! I also used the treadmill for a great workout!"

Reviewed on Jun 13, 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! (2,338 reviews)
"Hard to access from handicap parking"

Reviewed on Jun 13, 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! (1,022 reviews)
"The breakfast buffet was delicious and had a wide variety of options"

Reviewed on Jun 11, 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! (2,098 reviews)
"Great place to stay"

Reviewed on Jun 13, 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 (1,020 reviews)
"The website photos are straight up lies. The words that come to mind for the establishment are dilapidated, dank, poorly constructed, cheap. The ‘fitness center’ consists of two treadmills and a clearly broken cable machine (the cords were loosely strewn all over), half of the ‘breakfast’ was either ..."

Reviewed on Jun 12, 2026

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Carlton Inn Midway
See all 5,512 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.