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Chicago

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Chicago Flights as Low as $63

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

Frontier Airlines
Wed, Oct 14 - Wed, Oct 28
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 6 hours ago
$63
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 28, priced at $63 found 6 hours ago
Frontier Airlines
Thu, Oct 29 - Mon, Nov 16
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$85 Roundtrip, found 6 hours ago
$85
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Oct 29 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Nov 16, priced at $85 found 6 hours ago
Frontier Airlines
Wed, Oct 28 - Fri, Nov 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$95 Roundtrip, found 2 hours ago
$95
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Oct 28 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Fri, Nov 6, priced at $95 found 2 hours ago
Frontier Airlines
Thu, Oct 29 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$100 Roundtrip, found 18 hours ago
$100
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Thu, Oct 29 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Thu, Nov 19, priced at $100 found 18 hours ago
Frontier Airlines
Sat, Oct 17 - Sat, Oct 31
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$115 Roundtrip, found 9 hours ago
$115
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Sat, Oct 17 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, Oct 31, priced at $115 found 9 hours ago
Frontier Airlines
Wed, Nov 4 - Mon, Nov 16
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Nov 4 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Nov 16, priced at $118 found 2 days ago
Frontier Airlines
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 4 hours ago
$138
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Oct 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $138 found 4 hours ago
Bargain Flight
Mon, Sep 21 - Sat, Sep 26
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 Mon, Sep 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 26, priced at $177 found 1 day ago
Delta
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 4 hours ago
$217
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Oct 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $217 found 4 hours ago
American Airlines
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 4 hours ago
$217
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Oct 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $217 found 4 hours ago
Alaska Airlines
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 4 hours ago
$237
Roundtrip
found 4 hours ago
Select Alaska Airlines flight, departing Sat, Oct 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $237 found 4 hours ago
Bargain Flight
Wed, Sep 16 - Sat, Sep 26
SAN
San Diego Intl.
ORD
O'Hare Intl.
$258 Roundtrip, found 7 hours ago
$258
Roundtrip
found 7 hours ago
Select Bargain Flight flight, departing Wed, Sep 16 from San Diego Intl. to O'Hare Intl., returning Sat, Sep 26, priced at $258 found 7 hours ago
Southwest Airlines
Sat, Sep 26 - Sat, Oct 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$261 Roundtrip, found 18 hours ago
$261
Roundtrip
found 18 hours ago
Select Southwest Airlines flight, departing Sat, Sep 26 from Los Angeles Intl. to Midway Intl., returning Sat, Oct 3, priced at $261 found 18 hours ago
Southwest Airlines
Wed, Sep 16 - Sat, Sep 26
SAN
San Diego Intl.
MDW
Midway Intl.
$332 Roundtrip, found 12 hours ago
$332
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Sep 16 from San Diego Intl. to Midway Intl., returning Sat, Sep 26, priced at $332 found 12 hours ago
American Airlines
Fri, Sep 11 - Sun, Sep 13
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$377 Roundtrip, found 6 days ago
$377
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Sep 11 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sun, Sep 13, priced at $377 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Sep 21 - Sat, Sep 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$447 Roundtrip, found 1 day ago
$447
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Sep 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 26, priced at $447 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 October, 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 14 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 $63, 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 $63 right now, why wait?

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$63

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 ...
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Congress Plaza Hotel
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 ...
8/10 Very Good! (2,167 reviews)
"Clean and nice service was very helpful at front aswell"

Reviewed on Sep 6, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (888 reviews)
"We thoroughly enjoyed our stay at Kasa- check in instructions were clear and hassle free. The unit was spacious and clean, with a terrific view. Highly recommended!"

Reviewed on Sep 4, 2026

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Kasa Magnificent Mile 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 ...
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River Hotel
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
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Hampton Inn Chicago Downtown/Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
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Hilton Chicago
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (3,494 reviews)
"Amazing place to stay. Rooms were very well maintained, staff was friendly, and room was always cleaned on time. Didn't get a chance to get breakfast, but I did eat dinner at Stentons, and I can say it was lovely. Hotel is within walking distance to everything you could possibly dream of. I highly ..."

Reviewed on Sep 5, 2026

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Hyatt Regency Chicago
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
9.6/10 Exceptional! (4,739 reviews)
"The staff was great, they made the check in and check out process easy. The concierge, I believe his name is Alex was super helpful in giving me directions and making my check-in and checkout process extremely comfortable and easy. I appreciated his help very much."

Reviewed on Sep 6, 2026

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L7 Chicago by LOTTE
See all 5,387 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 ...
Get rates
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 ...
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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! (2,392 reviews)
"Great place to stay. Wonderful staff and clean rooms. Breakfast with many options to accommodate varied preferences."

Reviewed on Sep 3, 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 ...
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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! (2,208 reviews)
"Short overnight stay - so not a lot of exposure to the hotel amenities. Food/beverage voucher only useful at the restaurant which did not provide significant value. The real disheartening component was the fecal stain on the chair cushion. I did bring this to the facility’s attention, so I hope they ..."

Reviewed on Sep 6, 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 ...
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Carlton Inn Midway
See all 5,387 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.