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Chicago

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Chicago Flights as Low as $58

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

Frontier Airlines
Tue, Dec 10 - Wed, Dec 18
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Dec 10 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Dec 18, priced at $58 found 1 day ago
Frontier Airlines
Wed, Mar 5 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 6 days ago
$63
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Mar 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 5, priced at $63 found 6 days ago
Frontier Airlines
Tue, Dec 10 - Tue, Dec 17
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Dec 10 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 17, priced at $63 found 1 day ago
Frontier Airlines
Wed, Jan 8 - Wed, Jan 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jan 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jan 15, priced at $68 found 1 day ago
Frontier Airlines
Wed, Feb 12 - Sat, Feb 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 6 days ago
$73
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Feb 12 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Feb 15, priced at $73 found 6 days ago
Spirit Airlines
Sat, Dec 7 - Mon, Dec 9
LGA
LaGuardia
ORD
O'Hare Intl.
$77 Roundtrip, found 11 hours ago
$77
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Sat, Dec 7 from LaGuardia to O'Hare Intl., returning Mon, Dec 9, priced at $77 found 11 hours ago
Frontier Airlines
Thu, Jan 9 - Wed, Jan 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jan 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jan 15, priced at $78 found 1 day ago
Frontier Airlines
Mon, Dec 16 - Wed, Dec 18
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$83 Roundtrip, found 1 day ago
$83
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Dec 16 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Dec 18, priced at $83 found 1 day ago
Frontier Airlines
Thu, Dec 5 - Tue, Dec 10
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$84 Roundtrip, found 2 days ago
$84
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Dec 5 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 10, priced at $84 found 2 days ago
Frontier Airlines
Fri, Dec 6 - Sun, Dec 15
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$118 Roundtrip, found 5 days ago
$118
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Dec 6 from George Bush Intercontinental to O'Hare Intl., returning Sun, Dec 15, priced at $118 found 5 days ago
Delta
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 6 days ago
$132
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $132 found 6 days ago
American Airlines
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 6 days ago
$132
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $132 found 6 days ago
United
Wed, Jan 8 - Wed, Jan 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select United flight, departing Wed, Jan 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jan 15, priced at $137 found 1 day ago
Frontier Airlines
Sat, Nov 23 - Thu, Dec 5
IAH
George Bush Intercontinental
MDW
Midway Intl.
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Nov 23 from George Bush Intercontinental to Midway Intl., returning Thu, Dec 5, priced at $137 found 6 days ago
JetBlue Airways
Wed, Feb 19 - Mon, Mar 3
LGA
LaGuardia
ORD
O'Hare Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Feb 19 from LaGuardia to O'Hare Intl., returning Mon, Mar 3, priced at $198 found 1 day ago
Delta
Mon, Dec 16 - Tue, Dec 24
LGA
LaGuardia
MDW
Midway Intl.
$381 Roundtrip, found 4 days ago
$381
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Dec 16 from LaGuardia to Midway Intl., returning Tue, Dec 24, priced at $381 found 4 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 December, 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 $58, 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 $58 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$58

Last Minute Hotel Deals in Chicago

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $115 per night from Nov 24 to Nov 25
$115
includes taxes & fees
Nov 24 - Nov 25
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! (8,119 reviews)
"It is an old building so We were very pleased with how clean the rooms were. Tub drained slowly but did not affect our shower schedules. Radiator was a little confusing but it didn’t bother is because the weather was beautiful. Will stay again"

Reviewed on Nov 20, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $130 per night from Dec 22 to Dec 23
$130
includes taxes & fees
Dec 22 - Dec 23
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! (3,558 reviews)
"Great location. Rooms were tight but it doesn’t really matter for a weekend trip. Would stay here again."

Reviewed on Nov 19, 2024

River Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is $194 per night from Nov 25 to Nov 26
$194
includes taxes & fees
Nov 25 - Nov 26
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,011 reviews)
"The staff was very welcoming. The rooms were clean. Great location and view! Good cocktails!"

Reviewed on Nov 19, 2024

The Westin Michigan Avenue Chicago
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
The price is $119 per night from Dec 22 to Dec 23
$119
includes taxes & fees
Dec 22 - Dec 23
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
8.4/10 Very Good! (3,260 reviews)
"Great place"

Reviewed on Nov 19, 2024

Club Quarters Hotel, Central Loop, Chicago
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
The price is $137 per night from Dec 22 to Dec 23
$137
includes taxes & fees
Dec 22 - Dec 23
Stay at this 4-star 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 ...
8.6/10 Excellent! (2,751 reviews)
"Really great stay- the staff were really helpful from their valet to their suggestions for restaurants. Some element a bit dated but overall a great stay in a great location"

Reviewed on Nov 19, 2024

Eurostars Magnificent Mile
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
The price is $126 per night from Dec 22 to Dec 23
$126
includes taxes & fees
Dec 22 - Dec 23
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
7.8/10 Good! (1,271 reviews)
"Room is too small, and there is flash light to my window in the night"

Reviewed on Nov 19, 2024

Hotel Felix River North/Magnificent Mile
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 $135 per night from Dec 10 to Dec 11
$135
includes taxes & fees
Dec 10 - Dec 11
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 ...
8.2/10 Very Good! (3,214 reviews)
"Great!"

Reviewed on Nov 19, 2024

Embassy Suites by Hilton Chicago Downtown River North
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
The price is $128 per night from Nov 25 to Nov 26
$128
includes taxes & fees
Nov 25 - Nov 26
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (2,269 reviews)
"Friendly"

Reviewed on Nov 18, 2024

citizenM Chicago Downtown
See all 4,870 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 $84 per night from Nov 27 to Nov 28
$84
includes taxes & fees
Nov 27 - Nov 28
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! (1,007 reviews)
"I like everything"

Reviewed on Nov 20, 2024

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 $101 per night from Nov 24 to Nov 25
$101
includes taxes & fees
Nov 24 - Nov 25
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 ...
6.4/10 (1,003 reviews)
"It was okay, nothing special. The extended parking was $10 a day. An expense Travelocity did not tell us about."

Reviewed on Nov 18, 2024

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 $107 per night from Nov 28 to Nov 29
$107
includes taxes & fees
Nov 28 - Nov 29
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! (1,501 reviews)
"Rooms were clean and modern. Pool was nice and breakfast was delicious! Free parking is only included for the nights you’re staying there fyi."

Reviewed on Nov 18, 2024

Hampton Inn Chicago-O'Hare International Airport
Holiday Inn Chicago O'Hare Area, an IHG Hotel
Holiday Inn Chicago O'Hare Area, an IHG Hotel
3 out of 5
5615 North Cumberland Avenue, Chicago, IL
The price is $111 per night from Nov 24 to Nov 25
$111
includes taxes & fees
Nov 24 - Nov 25
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 ...
7.4/10 Good! (1,000 reviews)
"Great for train rides in and out of Chicago."

Reviewed on Nov 10, 2024

Holiday Inn Chicago O'Hare Area, an IHG Hotel
Loews Chicago O'Hare Hotel
Loews Chicago O'Hare Hotel
4.5 out of 5
5300 N River Rd, Rosemont, IL
The price is $158 per night from Dec 21 to Dec 22
$158
includes taxes & fees
Dec 21 - Dec 22
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 ...
9.2/10 Wonderful! (1,672 reviews)
"My room was extremely clean. Bed/pillows very comfortable. Staff was friendly and attentive. Hotel provides shuttle bus to the airport every 15 minutes. I highly recommend this hotel."

Reviewed on Nov 16, 2024

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 Nov 22 to Nov 23
$140
includes taxes & fees
Nov 22 - Nov 23
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 ...
6.6/10 (1,000 reviews)
Iffy
"The rooms do not look like what the pictures show on hotel.com. There are no dressers in the room and the bedding needs desperate attention. No mattress cover and covers are worn and as holes"

Reviewed on Nov 7, 2024

Carlton Inn Midway
See all 4,870 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.