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Chicago

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Chicago Flights as Low as $66

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

Frontier Airlines
Tue, Jun 9 - Wed, Jun 17
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$66 Roundtrip, found 6 hours ago
$66
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Jun 17, priced at $66 found 6 hours ago
Frontier Airlines
Tue, Jun 9 - Tue, Jun 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$66 Roundtrip, found 1 day ago
$66
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 16, priced at $66 found 1 day ago
Frontier Airlines
Tue, Jun 2 - Tue, Jun 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 13 hours ago
$68
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Jun 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 2, priced at $68 found 13 hours ago
Frontier Airlines
Wed, May 27 - Tue, Jun 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, May 27 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 2, priced at $68 just found
Frontier Airlines
Tue, Jun 9 - Tue, Jun 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, found 4 hours ago
$76
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 16, priced at $76 found 4 hours ago
JetBlue Airways
Tue, Jun 16 - Tue, Jun 23
BOS
Logan Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 5 days ago
$171
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Jun 16 from Logan Intl. to O'Hare Intl., returning Tue, Jun 23, priced at $171 found 5 days ago
United
Tue, Jun 16 - Tue, Jun 23
BOS
Logan Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 5 days ago
$171
Roundtrip
found 5 days ago
Select United flight, departing Tue, Jun 16 from Logan Intl. to O'Hare Intl., returning Tue, Jun 23, priced at $171 found 5 days ago
American Airlines
Tue, Jun 16 - Tue, Jun 23
BOS
Logan Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 5 days ago
$171
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Jun 16 from Logan Intl. to O'Hare Intl., returning Tue, Jun 23, priced at $171 found 5 days ago
Delta
Wed, May 27 - Tue, Jun 2
BOS
Logan Intl.
ORD
O'Hare Intl.
$192 Roundtrip, found 4 hours ago
$192
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, May 27 from Logan Intl. to O'Hare Intl., returning Tue, Jun 2, priced at $192 found 4 hours ago
Frontier Airlines
Wed, Jun 3 - Tue, Jun 9
BOS
Logan Intl.
MDW
Midway Intl.
$205 Roundtrip, found 4 days ago
$205
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Jun 3 from Logan Intl. to Midway Intl., returning Tue, Jun 9, priced at $205 found 4 days ago
JetBlue Airways
Mon, Jul 20 - Wed, Aug 5
BOS
Logan Intl.
ORD
O'Hare Intl.
$205 Roundtrip, found 4 hours ago
$205
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Mon, Jul 20 from Logan Intl. to O'Hare Intl., returning Wed, Aug 5, priced at $205 found 4 hours ago
American Airlines
Wed, Jul 1 - Wed, Aug 5
BOS
Logan Intl.
RFD
Greater Rockford
$246 Roundtrip, found 3 days ago
$246
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jul 1 from Logan Intl. to Greater Rockford, returning Wed, Aug 5, priced at $246 found 3 days ago
American Airlines
Sat, Jun 20 - Tue, Jun 23
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$331 Roundtrip, found 20 hours ago
$331
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Sat, Jun 20 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Tue, Jun 23, priced at $331 found 20 hours ago
Delta
Tue, Jul 14 - Tue, Jul 28
BHM
Birmingham Intl.
ORD
O'Hare Intl.
$367 Roundtrip, found 5 days ago
$367
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jul 14 from Birmingham Intl. to O'Hare Intl., returning Tue, Jul 28, priced at $367 found 5 days ago
American Airlines
Thu, Jul 2 - Sat, Jul 4
BHM
Birmingham Intl.
RFD
Greater Rockford
$406 Roundtrip, found 15 hours ago
$406
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Thu, Jul 2 from Birmingham Intl. to Greater Rockford, returning Sat, Jul 4, priced at $406 found 15 hours ago
Sun Country Airlines
Sat, Jul 4 - Thu, Aug 6
BOS
Logan Intl.
ORD
O'Hare Intl.
$505 Roundtrip, found 1 day ago
$505
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sat, Jul 4 from Logan Intl. to O'Hare Intl., returning Thu, Aug 6, priced at $505 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 June, 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 $66, 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 $66 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$66

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! (10,218 reviews)
Great location for a good price. Staff was helpful and the place was nice. It’s a little older building and shows a bit of wear here and there but not a bad spot at all. Overall worth the price!e

Reviewed on May 12, 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! (4,119 reviews)
El desayuno estuvo bien

Reviewed on May 12, 2026

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Hotel Riu Plaza Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,198 reviews)
Friendly staff and excellent location. Loved our 2 bed suite with 2 bathrooms and a kitchen! Would absolutely stay again!

Reviewed on May 11, 2026

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River Hotel
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! (4,298 reviews)
.

Reviewed on May 12, 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! (2,707 reviews)
The staff at Hotel Felix were kind, thoughtful, and genuinely helpful throughout my stay. The location is also a strong point — walking distance to a lot of great Chicago spots, which made getting around easy. My experience was somewhat diminished by the mandatory Urban Fee added at check-in. I understand ...

Reviewed on May 12, 2026

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Hotel Felix River North/Magnificent Mile
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (3,516 reviews)
The room was perfect. Staff attentive. I wasn’t a fan of the breakfast menu options so we opted not to eat at the adjoining restaurant. Hotel very clean.

Reviewed on May 11, 2026

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Club Quarters Hotel, Central Loop, Chicago
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (2,310 reviews)
Everything was amazing

Reviewed on May 12, 2026

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Holiday Inn Chicago Dwtn - The Mart by IHG
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (2,160 reviews)
Rooms a a little tired. Service at Toro is sub par

Reviewed on May 11, 2026

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Fairmont Chicago at Millennium Park
See all 5,548 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! (1,671 reviews)
Great hotel overall - check shuttle times - basic and economical, clean and well staffed.

Reviewed on May 10, 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! (1,412 reviews)
Very nice staff!!! Hotel smelled and looked clean! Stayed for two days when I left my room they cleaned our room with us asking and gave us towels

Reviewed on May 11, 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! (2,294 reviews)
Everything was great but the only problem was the pool and the hot tub. Both were cold and my kids and I couldn't enjoy it at all. Some measures need to be taken when customers experience these issues, given our financial commitment to rental and other.

Reviewed on May 11, 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! (1,012 reviews)
Nice and quiet. Clean. Safe

Reviewed on May 8, 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! (2,071 reviews)
Everything was top notch! Enjoy staying at this hotel. Everyone is very friendly and welcoming.

Reviewed on May 12, 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)
There are only two reasons to choose this hotel: its low price and its location—a 10-minute walk to the city train. Other than that, it falls short in many areas: poor management, understaffing (one person seems to handle everything), lack of attention to refilling breakfast items, weak wifi, and ...

Reviewed on May 6, 2026

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Carlton Inn Midway
See all 5,548 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.