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Cleveland to Chicago Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Cleveland to Chicago

Departure Arrival Travel dates Round-trip
CLE CHI Thu, Dec 18 - Wed, Jan 7 $85
CLE CHI Wed, Oct 1 - Mon, Oct 6 $209
CLE CHI Wed, Oct 1 - Mon, Oct 6 $209
CLE CHI Thu, Oct 2 - Mon, Oct 6 $214
CLE CHI Sun, Nov 9 - Sun, Nov 16 $237
CLE CHI Thu, Oct 9 - Sun, Oct 12 $522

Cleveland and Chicago airports and terminals

Airports in Cleveland OH, US
map of airports in Cleveland
  • 1

    Hopkins International (CLE)

    Distance from City Center: 9.5 miles

    Carriers for flights from CLE to CHI

    Carriers
    American Airlines, Cathay Pacific, Frontier Airlines, US Airways, United Airlines
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Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from CLE to ORD

    Terminal Carriers
    Terminal 1 US Airways, United Airlines
    Terminal 2 US Airways, United Airlines
    Terminal 3 American Airlines, Cathay Pacific, Frontier Airlines, US Airways
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Cheap flights from Cleveland to Chicago

Sun Mon Tue Wed Thu Fri Sat
1 2 3 4
5 6 7 8 9
$98
10 11
12 13
$98
14 15 16 17 18
19 20 21 22 23
$98
24 25
26 27 28 29 30 31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $119

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 122 reviews

O'Hare International Airport Map

Park & Fly - Includes up to 3 nights valet parking

...This O'Hare airport hotel is located in Terminal 2 and is within walking distance to all O'Hare Airport's domestic terminals.... More

Hotel only $137

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 42 reviews

6500 South Cicero Avenue Map

Exceptional Hotel Near Chicago Midway Airport Searching for hotels near the best sights in downtown Chicago?... More

Hotel only $144

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.6 / 5 14 reviews

6530 S. Cicero Avenue Map

Complimentary wired and Wi-Fi Internet Access

...Advance Purchase Rate online!The Hilton Garden Inn Chicago Midway Airport in Chicago is located on the Midway Hotel Center campus just two blocks south of the Chicago Midway Airport and the... More

Hotel only $135

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 17 reviews

6540 S. Cicero Ave. Map

Free On The HouseT hot breakfast, Wi-Fi

...And no matter what time your flight got in or is going out, we're here to pick you up or drop you off.... land here and let your vacation take off...welcome to the Hampton Inn Chicago-Midway... More

Hotel only $179

Chicago Marriott Midway

3 stars
3.7 / 5 7 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

...WiFi-equipped guest rooms at our Chicago Midway Airport hotel are recently renovated and offer soundproof windows, 32" flat-screen TVs and room service.... Perfect for business travel and... More

Hotel only $109

Sheraton Chicago O’Hare Airport Hotel

4 stars
4.0 / 5 109 reviews

6501 N. Mannheim Road Map

Save 40% on your stay

...Complimentary shuttle service to and from O'Hare Airport is available 24 hours a day.... Our all-suite hotel is conveniently located minutes from O'Hare International Airport, Donald E. Stephens... More

October

Cheapest weekend flights in October from Cleveland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 9 Cleveland (CLE) Chicago (ORD) Frontier Airlines $98
Earn $0.98
Return Mon, Oct 13 Chicago (ORD) Cleveland (CLE) Frontier Airlines

Lowest roundtrip airfare in October from Cleveland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 9 Cleveland (CLE) Chicago (ORD) Frontier Airlines $98
Earn $0.98
Return Mon, Oct 13 Chicago (ORD) Cleveland (CLE) Frontier Airlines

Best one-week trip in October from Cleveland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Oct 19 Cleveland (CLE) Chicago (ORD) Frontier Airlines $127
Earn $1.27
Return Sun, Oct 26 Chicago (ORD) Cleveland (CLE) Frontier Airlines
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November

Cheapest weekend flights in November from Cleveland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 6 Cleveland (CLE) Chicago (ORD) Frontier Airlines $98
Earn $0.98
Return Mon, Nov 10 Chicago (ORD) Cleveland (CLE) Frontier Airlines

Lowest roundtrip airfare in November from Cleveland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Nov 5 Cleveland (CLE) Chicago (ORD) Frontier Airlines $98
Earn $0.98
Return Mon, Nov 10 Chicago (ORD) Cleveland (CLE) Frontier Airlines

Best one-week trip in November from Cleveland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Nov 9 Cleveland (CLE) Chicago (ORD) Frontier Airlines $127
Earn $1.27
Return Sun, Nov 16 Chicago (ORD) Cleveland (CLE) Frontier Airlines
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December

Cheapest weekend flights in December from Cleveland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Dec 4 Cleveland (CLE) Chicago (ORD) Frontier Airlines $102
Earn $1.02
Return Sun, Dec 7 Chicago (ORD) Cleveland (CLE) Frontier Airlines

Lowest roundtrip airfare in December from Cleveland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Dec 18 Cleveland (CLE) Chicago (ORD) Frontier Airlines $85
Earn $0.85
Return Wed, Jan 7 Chicago (ORD) Cleveland (CLE) Frontier Airlines
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Flights to Chicago

Cleveland International Airport

You can quickly and easily book cheap flights from Cleveland with Orbitz.com. The Cleveland Hopkins International Airport is situated approximately nine miles southwest of the city's central business district. Both domestic and international flights are provided by the airlines serving the Cleveland airport, including American Airlines, Delta Air Lines, Southwest Airlines, United Airlines, and US Airways. The airport was the first in North America to have an airport-to-downtown transit connection. It was also the first airport to have an air traffic control tower and airfield lighting system.

Cleveland Airport Parking

Parking is available at the Cleveland International Airport 24/7. Color-coded cards are available to assist visitors in locating their vehicles in the on-site parking garages. Parking garage tickets are dispensed automatically at garage entrances. Acceptable forms of payment include personal checks, cash, and credit cards. The airport operates an economy shuttle parking lot at a rate of $8.00 per day. Smarte Cartes are also available at the airport at a rate of $2.00.

Cleveland Airport Transportation

Travelers using the Hopkins International Airport can take advantage of its connection to the Cleveland Rapid Transit system. In addition, the airport is also served by a dedicated taxi service comprised of 75 vehicles for the convenience of travelers. Rental car services are offered at a consolidated facility off the airport grounds. Transportation to and from the Hopkins International Airport can be quickly arranged through Orbitz.com.

Cleveland Airport Restaurants

Travelers who are looking for a snack or meal prior to boarding their flight will find that the Cleveland airport offers a variety of dining options, including Cinnabon, Dunkin Donuts, Auntie Anne's Soft Pretzels, Sbarro, and Subway. Finding breakfast or even a quick lunch or dinner is always fast and easy. Using Orbitz.com will help you to locate cheap flights from Cleveland and help you to find and book the best rates on all your ground transportation needs.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Interesting facts about flights from Cleveland to Chicago

    • 25 direct flights are operating from Cleveland to Chicago today.
    • Today's average time for a direct flight is 1h 23m.
    • American Airlines flight 4274 (1:05 AM GMT, Embraer 175) is today's earliest available flight from Cleveland to Chicago.
    • United Airlines flight 5288 (3:51 PM GMT, Embraer RJ145) is today's latest available flight from Cleveland to Chicago.
    • Today's shortest direct flight from Cleveland to Chicago (American Airlines flight 4274, Embraer 175) takes 1h 15m.
    • Today's longest direct flight from Cleveland to Chicago (US Airways flight 4453, Embraer RJ140) takes 1h 32m.
    • Flights from Hopkins International (CLE) to Midway Airport (MDW), O'Hare Airport (ORD) are available for this route.

Aircraft options between Cleveland and Chicago

Equipment Carrier
Embraer 170 United Airlines, US Airways
Boeing 737-700 Passenger United Airlines, US Airways
Boeing 757-200 Passenger United Airlines, US Airways
Boeing 757-300 Passenger United Airlines, US Airways
Embraer RJ135/RJ140/RJ145 United Airlines, US Airways
Airbus Industrie A319 United Airlines, US Airways
Canadair Regional Jet 700 American Airlines, US Airways, United Airlines
Airbus Industrie A320 United Airlines, US Airways, Frontier Airlines
Embraer RJ140 American Airlines, US Airways
Boeing 737-900 Passenger United Airlines, US Airways
Boeing 737-800 Passenger United Airlines, US Airways
Canadair Regional Jet United Airlines, US Airways
Embraer RJ145 American Airlines, US Airways, United Airlines, Cathay Pacific
Embraer 175 American Airlines, US Airways