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Chicago

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Chicago Flights as Low as $106

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

Frontier Airlines
Tue, Sep 1 - Sat, Sep 5
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$106 Roundtrip, found 5 days ago
$106
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Sep 1 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Sep 5, priced at $106 found 5 days ago
Frontier Airlines
Mon, Sep 28 - Mon, Oct 5
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$118 Roundtrip, found 8 hours ago
$118
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Oct 5, priced at $118 found 8 hours ago
Frontier Airlines
Mon, Aug 31 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 3 days ago
$120
Roundtrip
found 3 days 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 3 days ago
Frontier Airlines
Wed, Sep 16 - Tue, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$123 Roundtrip, found 9 hours ago
$123
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $123 found 9 hours ago
Bargain Flight
Fri, Aug 14 - Sun, Aug 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Fri, Aug 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 16, priced at $177 found 1 day ago
Delta
Wed, Sep 30 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$192 Roundtrip, found 8 hours ago
$192
Roundtrip
found 8 hours ago
Select Delta flight, departing Wed, Sep 30 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 30, priced at $192 found 8 hours ago
Frontier Airlines
Tue, Jul 14 - Tue, Jul 21
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$207 Roundtrip, found 4 days ago
$207
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Jul 14 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Jul 21, priced at $207 found 4 days ago
Delta
Wed, Aug 26 - Sat, Sep 5
DAL
Love Field
ORD
O'Hare Intl.
$226 Roundtrip, found 6 days ago
$226
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Aug 26 from Love Field to O'Hare Intl., returning Sat, Sep 5, priced at $226 found 6 days ago
American Airlines
Tue, Jul 7 - Thu, Jul 9
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$273 Roundtrip, found 3 hours ago
$273
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Jul 7 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Jul 9, priced at $273 found 3 hours ago
Frontier Airlines
Tue, Oct 13 - Wed, Oct 21
LAX
Los Angeles Intl.
MDW
Midway Intl.
$290 Roundtrip, found 1 hour ago
$290
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Oct 13 from Los Angeles Intl. to Midway Intl., returning Wed, Oct 21, priced at $290 found 1 hour ago
Contour Airlines
Tue, Aug 25 - Thu, Aug 27
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$294 Roundtrip, found 12 hours ago
$294
Roundtrip
found 12 hours ago
Select Contour Airlines flight, departing Tue, Aug 25 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Aug 27, priced at $294 found 12 hours ago
Delta
Tue, Oct 13 - Wed, Oct 14
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 Wed, Oct 14, priced at $311 found 1 day ago
American Airlines
Wed, Jul 1 - Sat, Jul 4
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$311 Roundtrip, found 12 hours ago
$311
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Wed, Jul 1 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sat, Jul 4, priced at $311 found 12 hours ago
Alaska Airlines
Tue, Oct 20 - Tue, Oct 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$315 Roundtrip, found 8 hours ago
$315
Roundtrip
found 8 hours ago
Select Alaska Airlines flight, departing Tue, Oct 20 from Los Angeles Intl. to O'Hare Intl., returning Tue, Oct 27, priced at $315 found 8 hours 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 - Sun, Jul 19
LAX
Los Angeles Intl.
RFD
Greater Rockford
$340 Roundtrip, found 6 days ago
$340
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sun, Jul 19, priced at $340 found 6 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 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 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 $106, 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 $106 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$118

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! (10,286 reviews)
"This is the second time I’ve stayed at this property. It is conveniently located and the rooms facing the lake have a gorgeous view (request lake view). The room lighting was poor, and I missed having a table on each side of the bed."

Reviewed on Jun 16, 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! (2,676 reviews)
"Aside from the liberal marketing and CNN programming everywhere, it was a nice experience."

Reviewed on Jun 15, 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! (1,592 reviews)
"Clean room staff nice"

Reviewed on Jun 15, 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! (2,346 reviews)
"I really can't write a comprehensive review because we only stayed here for a short layover. Arrived at midnight and left at 5:30. I can, however, say that the hotel was clean, check-in was efficient and location was great as we were able to walk from our plane to the hotel in under 10 minutes. Just ..."

Reviewed on Jun 16, 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! (1,611 reviews)
"It was so relaxing. Older room but has been upgraded and was clean. Restaurant had great food."

Reviewed on Jun 15, 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! (4,434 reviews)
"For it being my first time Chicago, the staff were so welcoming and gave me a lot of great pointers for food, entertainment and helpful with getting settled. The room itself was super clean and I would definitely book this hotel again!"

Reviewed on Jun 16, 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! (2,800 reviews)
"Rooms are SUPER small. Just imagine paying almost $400 for ONE night for -no pool -outdated hallways and elevators -3rd party valet service so the front desk will not help you at all with them -one one valet (who was so sweet) but it was a 45 min wait if you wanted your car -no microwave -no breakfast ..."

Reviewed on Jun 15, 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! (3,109 reviews)
"Our hotel room was very nice and staff made it easy to check in. The only downside to the hotel is the swimming pool. It was large and deep but kind of scary due to all the rust on the walls."

Reviewed on Jun 15, 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! (1,731 reviews)
"I stayed here for a night but it was most horrible stay of my life. I arrived hotel at 1 am (Late night). They gave me key and i intered in room. When I entered, I saw room was already used and not cleaned. Somebody ate food there and remaining food and empty water bottles lying there. I also found ..."

Reviewed on Jun 14, 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! (1,514 reviews)
"Pool was dirty, hair all over the floor and in the pool"

Reviewed on Jun 16, 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! (2,342 reviews)
"I had a great stay here. The staff was helpful, and the shuttle made it extra convenient. The breakfast was delicious also"

Reviewed on Jun 15, 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! (1,024 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 ...
9.6/10 Exceptional! (2,104 reviews)
"The room was very clean, bed was very comfortable. This is by far the best hotel I’ve stayed in."

Reviewed on Jun 15, 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 (1,023 reviews)
"Kinda what you would expect from a motel, however we found left over food in our room"

Reviewed on Jun 14, 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.