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Chicago

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Chicago Flights as Low as $77

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

Delta
Mon, May 26 - Tue, May 27
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$77 Roundtrip, found 5 days ago
$77
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, May 26 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Tue, May 27, priced at $77 found 5 days ago
Frontier Airlines
Wed, May 7 - Sun, May 11
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$81 Roundtrip, found 4 days ago
$81
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, May 7 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sun, May 11, priced at $81 found 4 days ago
Frontier Airlines
Tue, May 6 - Sun, May 11
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$82 Roundtrip, found 4 days ago
$82
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, May 6 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sun, May 11, priced at $82 found 4 days ago
American Airlines
Tue, May 27 - Thu, May 29
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$84 Roundtrip, found 6 days ago
$84
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, May 27 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Thu, May 29, priced at $84 found 6 days ago
Frontier Airlines
Wed, May 7 - Sun, May 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 4 days ago
$88
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, May 7 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, May 11, priced at $88 found 4 days ago
American Airlines
Tue, May 27 - Thu, May 29
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$93 Roundtrip, found 6 days ago
$93
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, May 27 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Thu, May 29, priced at $93 found 6 days ago
United
Tue, May 27 - Thu, May 29
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$101 Roundtrip, found 6 days ago
$101
Roundtrip
found 6 days ago
Select United flight, departing Tue, May 27 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Thu, May 29, priced at $101 found 6 days ago
Spirit Airlines
Sun, May 25 - Sun, May 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$106 Roundtrip, found 1 day ago
$106
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, May 25 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, May 25, priced at $106 found 1 day ago
Sun Country Airlines
Thu, May 22 - Mon, May 26
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$169 Roundtrip, found 8 hours ago
$169
Roundtrip
found 8 hours ago
Select Sun Country Airlines flight, departing Thu, May 22 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, May 26, priced at $169 found 8 hours ago
Delta
Tue, Jul 1 - Sat, Jul 5
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 1 from Minneapolis - St. Paul Intl. to Midway Intl., returning Sat, Jul 5, priced at $179 found 1 day ago
JetBlue Airways
Sat, May 31 - Tue, Jun 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$318 Roundtrip, found 1 day ago
$318
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, May 31 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 10, priced at $318 found 1 day ago
United
Thu, May 8 - Wed, Jun 11
MLM
General Francisco Mujica Intl.
ORD
O'Hare Intl.
$338 Roundtrip, found 11 hours ago
$338
Roundtrip
found 11 hours ago
Select United flight, departing Thu, May 8 from General Francisco Mujica Intl. to O'Hare Intl., returning Wed, Jun 11, priced at $338 found 11 hours ago
Frontier Airlines
Wed, Jul 9 - Sun, Aug 3
MLM
General Francisco Mujica Intl.
MDW
Midway Intl.
$417 Roundtrip, found 1 day ago
$417
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jul 9 from General Francisco Mujica Intl. to Midway Intl., returning Sun, Aug 3, priced at $417 found 1 day ago
Viva Aerobus
Fri, May 9 - Thu, Jun 5
MLM
General Francisco Mujica Intl.
ORD
O'Hare Intl.
$429 Roundtrip, found 2 days ago
$429
Roundtrip
found 2 days ago
Select Viva Aerobus flight, departing Fri, May 9 from General Francisco Mujica Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $429 found 2 days ago
Volaris
Sat, Jul 12 - Mon, Aug 4
MLM
General Francisco Mujica Intl.
MDW
Midway Intl.
$524 Roundtrip, found 1 day ago
$524
Roundtrip
found 1 day ago
Select Volaris flight, departing Sat, Jul 12 from General Francisco Mujica Intl. to Midway Intl., returning Mon, Aug 4, priced at $524 found 1 day ago
Aeromexico
Mon, Jul 14 - Mon, Aug 11
MLM
General Francisco Mujica Intl.
MDW
Midway Intl.
$650 Roundtrip, found 1 day ago
$650
Roundtrip
found 1 day ago
Select Aeromexico flight, departing Mon, Jul 14 from General Francisco Mujica Intl. to Midway Intl., returning Mon, Aug 11, priced at $650 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 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 $77, 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 $77 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$81

Last Minute Hotel Deals in 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
The price is $193 per night from May 11 to May 12
$193
includes taxes & fees
May 11 - May 12
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (3,954 reviews)
"Excellent location and very clean. Traveled solo with 2 kids and felt safe. Valet parking option needs better signage. Would absolutely stay here again."

Reviewed on Apr 27, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $189 per night from May 27 to May 28
$189
includes taxes & fees
May 27 - May 28
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,729 reviews)
"Amazing stay and people"

Reviewed on Apr 28, 2025

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is $188 per night from May 11 to May 12
$188
includes taxes & fees
May 11 - May 12
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 ...
8.8/10 Excellent! (2,167 reviews)
"Everything excellent just in our room we struggled with hot water… but everything ok"

Reviewed on Apr 28, 2025

Hilton Chicago/Magnificent Mile Suites
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
The price is $235 per night from Apr 30 to May 1
$235
includes taxes & fees
Apr 30 - May 1
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and ...
"Great Customer Service! Great Stay! close to downtown Chicago !"

Reviewed on Apr 27, 2025

Swissotel - Chicago
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $164 per night from May 8 to May 9
$164
includes taxes & fees
May 8 - May 9
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (4,101 reviews)
"Thus property was beautiful, very clean, friendly staff and there was free coffee. Amazing views made it even better. We walked across the street to the River Walk and down the block to a boat tour. We also walked to a bar and a restaurant downtown. If we go back to Chicago, we would definitely stay ..."

Reviewed on Apr 27, 2025

River Hotel
The Allegro Royal Sonesta Hotel Chicago Loop
The Allegro Royal Sonesta Hotel Chicago Loop
4 out of 5
171 W Randolph St, Chicago, IL
The price is $232 per night from May 11 to May 12
$232
includes taxes & fees
May 11 - May 12
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
8.8/10 Excellent! (1,672 reviews)
"Lovely old hotel well maintained. Close to so many sights."

Reviewed on Apr 27, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
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
The price is $143 per night from May 11 to May 12
$143
includes taxes & fees
May 11 - May 12
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,021 reviews)
"Great stay."

Reviewed on Apr 28, 2025

Crowne Plaza Chicago West Loop by IHG
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
4.5 out of 5
200 North Columbus Drive, Chicago, IL
The price is $240 per night from May 2 to May 3
$240
includes taxes & fees
May 2 - May 3
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,686 reviews)
"-"

Reviewed on Apr 29, 2025

Fairmont Chicago at Millennium Park
See all 5,112 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
2.5 out of 5
2951 Touhy Ave, Elk Grove Village, IL
The price is $86 per night from May 12 to May 13
$86
includes taxes & fees
May 12 - May 13
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 ...
7.8/10 Good! (1,171 reviews)
"Desk manager at night time friendly."

Reviewed on Apr 24, 2025

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
The price is $102 per night from May 4 to May 5
$102
includes taxes & fees
May 4 - May 5
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
6.8/10 (1,002 reviews)
"I loved the breakfast! The only downside is that the temp was controlled with a energy saving thermostat that no matter how low I put the temp, it just wouldnt cool enough for my liking."

Reviewed on Apr 25, 2025

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
The price is $119 per night from May 4 to May 5
$119
includes taxes & fees
May 4 - May 5
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 ...
9/10 Wonderful! (1,853 reviews)
"Arrived late after a rough travel day. Staff was lovely and even found some fresh fruit for us."

Reviewed on Apr 29, 2025

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
The price is $121 per night from May 4 to May 5
$121
includes taxes & fees
May 4 - May 5
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
7.6/10 Good! (1,004 reviews)
"Great place to be"

Reviewed on Apr 19, 2025

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
The price is $238 per night from May 2 to May 3
$238
includes taxes & fees
May 2 - May 3
Stay at this 4.5-star luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the ...
9.4/10 Exceptional! (1,795 reviews)
"The bed was so comfortable, the shower was therapeutic, the in-room breakfast was delicious!"

Reviewed on Apr 26, 2025

Loews Chicago O'Hare Hotel
Carlton Inn Midway
Carlton Inn Midway
2 out of 5
4944 S Archer Ave, Chicago, IL
The price is $140 per night from Apr 30 to May 1
$140
includes taxes & fees
Apr 30 - May 1
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 ...
6.4/10 (1,006 reviews)
Pleasantly Surprised
"Better than reviews led me to believe. Comfortable and clean"

Reviewed on Apr 28, 2025

Carlton Inn Midway
See all 5,112 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.