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Chicago

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Chicago Flights as Low as $72

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

Frontier Airlines
Tue, Apr 28 - Tue, May 5
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$72 Roundtrip, found 1 hour ago
$72
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Apr 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, May 5, priced at $72 found 1 hour ago
Frontier Airlines
Wed, May 6 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 6 hours ago
$72
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, May 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 12, priced at $72 found 6 hours ago
Frontier Airlines
Tue, Apr 14 - Sat, Apr 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, found 3 days ago
$76
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Apr 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Apr 25, priced at $76 found 3 days ago
Frontier Airlines
Wed, May 6 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$81 Roundtrip, found 6 hours ago
$81
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, May 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 12, priced at $81 found 6 hours ago
Spirit Airlines
Wed, May 6 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$99 Roundtrip, found 6 hours ago
$99
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Wed, May 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 12, priced at $99 found 6 hours ago
Spirit Airlines
Wed, Apr 22 - Tue, Apr 28
LGA
LaGuardia
ORD
O'Hare Intl.
$110 Roundtrip, found 4 days ago
$110
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Apr 22 from LaGuardia to O'Hare Intl., returning Tue, Apr 28, priced at $110 found 4 days ago
Bargain Flight
Sun, Jun 14 - Thu, Jun 18
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 16 hours ago
$167
Roundtrip
found 16 hours ago
Select Bargain Flight flight, departing Sun, Jun 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Jun 18, priced at $167 found 16 hours ago
Frontier Airlines
Wed, Apr 22 - Tue, May 5
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$190 Roundtrip, found 3 days ago
$190
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Apr 22 from San Francisco Intl. to O'Hare Intl., returning Tue, May 5, priced at $190 found 3 days ago
American Airlines
Sat, Apr 25 - Mon, Apr 27
LGA
LaGuardia
ORD
O'Hare Intl.
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Apr 25 from LaGuardia to O'Hare Intl., returning Mon, Apr 27, priced at $197 found 4 days ago
Delta
Tue, Jul 28 - Mon, Aug 10
LGA
LaGuardia
ORD
O'Hare Intl.
$197 Roundtrip, found 21 hours ago
$197
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Jul 28 from LaGuardia to O'Hare Intl., returning Mon, Aug 10, priced at $197 found 21 hours ago
Alaska Airlines
Tue, Apr 28 - Tue, May 5
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$225 Roundtrip, found 1 day ago
$225
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Apr 28 from San Francisco Intl. to O'Hare Intl., returning Tue, May 5, priced at $225 found 1 day ago
Frontier Airlines
Sat, Apr 25 - Fri, May 8
SFO
San Francisco Intl.
MDW
Midway Intl.
$230 Roundtrip, found 2 days ago
$230
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Apr 25 from San Francisco Intl. to Midway Intl., returning Fri, May 8, priced at $230 found 2 days ago
American Airlines
Mon, Apr 27 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$236 Roundtrip, found 1 day ago
$236
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Apr 27 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, May 1, priced at $236 found 1 day ago
Hawaiian Airlines
Mon, Apr 13 - Tue, Apr 21
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$251 Roundtrip, found 1 day ago
$251
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Mon, Apr 13 from San Francisco Intl. to O'Hare Intl., returning Tue, Apr 21, priced at $251 found 1 day ago
Delta
Tue, Jun 16 - Wed, Jun 17
LGA
LaGuardia
MDW
Midway Intl.
$431 Roundtrip, found 1 day ago
$431
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 16 from LaGuardia to Midway Intl., returning Wed, Jun 17, priced at $431 found 1 day ago
JetBlue Airways
Wed, May 6 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$442 Roundtrip, found 6 hours ago
$442
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Wed, May 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 12, priced at $442 found 6 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 April, 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 $72, 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 $72 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$62

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! (9,968 reviews)
Nice room, a bit disturbed I had to pay a safety fee of$25.00 for each day of my stay.

Reviewed on Mar 20, 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! (3,569 reviews)
Staff was friendly, rooms were clean and breakfast was delicious

Reviewed on Mar 19, 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! (5,749 reviews)
The location was great, near plenty of restaurants and shopping. The room was a great layout plenty of space.

Reviewed on Mar 19, 2026

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Embassy Suites by Hilton Chicago Downtown River North
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! (3,943 reviews)
The bathrooms need updating. The shower floor is chipping. There are cracks between the wall and floor of shower. There is water damage on the base of bathroom door. Which is "bubbling" up. One can see that instead of replacing door. It has been painted over repeatedly. The wall socket near the nightstand ...

Reviewed on Mar 20, 2026

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Hilton Chicago/Magnificent Mile Suites
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! (2,228 reviews)
The hotel had no electricity upon arrival, inexplicably as there were no severe weather conditions. I was handed two glow sticks to be able to guide my way around the hotel and my room. You can’t make this stuff up. The fact that there was nothing provided to compensate for the matter (discount, ...

Reviewed on Mar 19, 2026

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Hilton Chicago O'Hare Airport
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,740 reviews)
The staff was super nice, hotel was quiet and room was comfy. Very close to navy pier, within walking distance. Would be a great hotel for the summertime.

Reviewed on Mar 20, 2026

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The Wade
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (3,142 reviews)
Convenient location, good rooms, good wifi

Reviewed on Mar 19, 2026

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Aloft Chicago Mag Mile
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (3,315 reviews)
It was ok

Reviewed on Mar 18, 2026

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Eurostars Magnificent Mile
See all 5,533 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! (1,625 reviews)
It's a decent place. Quite old. Good for a 1-2 day stay. For the price, it's good. It's not a Marriott or Hilton, so that standard is different. Breakfast was basically just some waffles and bread.

Reviewed on Mar 19, 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! (1,306 reviews)
Clean room, nice staff

Reviewed on Mar 19, 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! (2,242 reviews)
Great staff, airport shuttle,

Reviewed on Mar 20, 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! (1,003 reviews)
Good

Reviewed on Mar 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! (1,989 reviews)
Everything was great

Reviewed on Mar 19, 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 (1,002 reviews)
Room is dirty, bad cleaning. Gave us a single bedroom as we ordered double bedroom online, and they refused to give any refund. Suck motel overall.

Reviewed on Mar 18, 2026

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Carlton Inn Midway
See all 5,533 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.