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Orlando 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 Orlando to Chicago

Departure Arrival Travel dates Round-trip
ORL CHI Tue, Oct 28 - Wed, Nov 5 $150
ORL CHI Sat, Dec 20 - Mon, Jan 5 $215
ORL CHI Thu, Oct 2 - Tue, Oct 7 $244
ORL CHI Wed, Dec 24 - Wed, Dec 31 $255
ORL CHI Wed, Dec 24 - Mon, Jan 5 $259
ORL CHI Fri, Oct 3 - Tue, Oct 7 $260
ORL CHI Fri, Jan 16 - Mon, Jan 19 $266
ORL CHI Tue, Oct 28 - Wed, Nov 5 $401
ORL CHI Thu, Jan 15 - Fri, Jan 16 $483
ORL CHI Thu, Dec 25 - Mon, Dec 29 $1,563

Orlando and Chicago airports and terminals

Airports in Orlando FL, US
map of airports in Orlando
  • 1

    Orlando Airport (MCO)

    Distance from City Center: 14.5 miles

    Carriers for flights from MCO to CHI

    Carriers
    AirTran Airways, American Airlines, Cathay Pacific, 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

    Carriers for flights from ORL to MDW

    Carriers
    AirTran Airways
  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from ORL to ORD

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

Sun Mon Tue Wed Thu Fri Sat
1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28
$150
29 30 31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $139

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 123 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 Orlando to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Oct 31 Orlando (MCO) Chicago (ORD) Spirit Airlines $175
Earn $1.75
Return Mon, Nov 3 Chicago (ORD) Orlando (MCO) Spirit Airlines

Lowest roundtrip airfare in October from Orlando to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 28 Orlando (MCO) Chicago (ORD) Spirit Airlines $150
Earn $1.50
Return Wed, Nov 5 Chicago (ORD) Orlando (MCO) Spirit Airlines

Best one-week trip in October from Orlando to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Oct 22 Orlando (MCO) Chicago (ORD) Spirit Airlines $211
Earn $2.11
Return Wed, Oct 29 Chicago (ORD) Orlando (MCO) Spirit Airlines
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November

Cheapest weekend flights in November from Orlando to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 6 Orlando (MCO) Chicago (ORD) Spirit Airlines $225
Earn $2.25
Return Sun, Nov 9 Chicago (ORD) Orlando (MCO) Spirit Airlines

Lowest roundtrip airfare in November from Orlando to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Nov 3 Orlando (MCO) Chicago (ORD) Spirit Airlines $175
Earn $1.75
Return Mon, Nov 10 Chicago (ORD) Orlando (MCO) Spirit Airlines

Best one-week trip in November from Orlando to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Nov 3 Orlando (MCO) Chicago (ORD) Spirit Airlines $175
Earn $1.75
Return Mon, Nov 10 Chicago (ORD) Orlando (MCO) Spirit Airlines
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December

Cheapest weekend flights in December from Orlando to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Dec 4 Orlando (MCO) Chicago (ORD) Spirit Airlines $175
Earn $1.75
Return Mon, Dec 8 Chicago (ORD) Orlando (MCO) Spirit Airlines

Lowest roundtrip airfare in December from Orlando to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Dec 5 Orlando (MCO) Chicago (ORD) Spirit Airlines $155
Earn $1.55
Return Tue, Dec 9 Chicago (ORD) Orlando (MCO) Spirit Airlines

Best one-week trip in December from Orlando to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Dec 3 Orlando (MCO) Chicago (ORD) Spirit Airlines $165
Earn $1.65
Return Wed, Dec 10 Chicago (ORD) Orlando (MCO) Spirit Airlines
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Flights from Orlando to Chicago

Orlando International Airport

Locating cheap flights from Orlando can be simple with Orbitz.com. The site allows travelers to search a variety of airlines at one time in order to locate the best deals on tickets. Orlando International Airport is located just nine miles southeast of downtown Orlando on Airport Boulevard. Forty-three airlines serve the Orlando International Airport, including AirTran, Continental, United and World Atlantic. Orbitz.com provides air tickets for the majority of these airlines, which is perfect for travelers on a budget.

Parking at Orlando International Airport

Orlando International Airport offers a variety of parking options. The short-term cell phone lot is free for dropping off and picking up passengers. Garage and lot parking is available for both short-term and long-term use and is charged by the day. Valet parking is available for an additional charge and they offer car detailing at a flat rate.

Transportation to the Airport

Orbitz.com can provide information on rental cars in the area. Rental fees may vary depending on the vehicle that you rent. Metered taxi services are available, and many hotels offer free shuttle services to and from the airport. Limos are available to rent by the hour, and the local bus is available for a flat fee depending on your location of origin.

Restaurants at Orlando International

Orlando International Airport offers a variety of options for travelers that want to grab a snack or a meal before boarding the flight. Restaurants include Krispy Kreme and Starbucks, which features a variety of gourmet coffees and pastries. Orbitz.com is perfect for travelers looking for cheap flights from Orlando.

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 Orlando to Chicago

    • 13 direct flights are operating from Orlando to Chicago today.
    • Today's average time for a direct flight is 2h 48m.
    • United Airlines flight 1553 (3:05 AM GMT, Boeing 737-800 Passenger) is today's earliest available flight from Orlando to Chicago.
    • AirTran Airways flight 143 (3:40 PM GMT, Boeing 717) is today's latest available flight from Orlando to Chicago.
    • Today's shortest direct flight from Orlando to Chicago (American Airlines flight 1221, Boeing 737-800 Passenger) takes 2h 45m.
    • Today's longest direct flight from Orlando to Chicago (American Airlines flight 1693, Boeing 737-800 Passenger) takes 2h 55m.
    • Flights from Orlando Airport (MCO) to Midway Airport (MDW), O'Hare Airport (ORD) are available for this route.

Aircraft options between Orlando and Chicago

Equipment Carrier
Boeing 717 AirTran Airways
Boeing 737-700 Passenger United Airlines, US Airways, AirTran Airways
Boeing 757-200 Passenger United Airlines, US Airways
Boeing 757-300 Passenger United Airlines
Boeing 737-900 Passenger United Airlines, US Airways
Airbus Industrie A319 United Airlines, US Airways
Boeing 737-800 Passenger American Airlines, US Airways, United Airlines, Cathay Pacific
McDonnell Douglas MD-80 American Airlines, US Airways
McDonnell Douglas MD-83 American Airlines, US Airways
Airbus Industrie A320 United Airlines, US Airways