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Flights from Orlando to Chicago Starting at $19

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • One way
  • Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from Orlando to Chicago?

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Find cheap airlines flights from Orlando to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines
From $19
Spirit Airlines
From $20
Southwest Airlines
From $55
Allegiant Air
From $81
United Airlines
From $82
Delta Air Lines
From $87
Sun Country Airlines
From $89
American Airlines
From $109
Jetblue Airways
From $160
Silver Airways
From $192
ANA airlines

Find more flights and airlines

Alternative Cheap Routes from Orlando to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Orlando to Chicago.

  • Cheapest
    Frontier Airlines
    MCO
    21:39
    3h 4m
    Direct
    ORD
    23:43
    Orlando International Airport - O'Hare International Airport
    Fri, Apr 12Frontier Airlines
    $19
  • Frontier Airlines
    MCO
    12:15
    3h 6m
    Direct
    MDW
    14:21
    Orlando International Airport - Midway International Airport
    Tue, Apr 9Frontier Airlines
    $37
  • Allegiant Air
    SFB
    06:30
    2h 43m
    Direct
    RFD
    08:13
    Orlando Sanford International Airport - Chicago Rockford International Airport
    Mon, May 6Allegiant Air
    $81
  • Allegiant Air
    SFB
    06:30
    2h 43m
    Direct
    RFD
    08:13
    Orlando Sanford International Airport - Chicago Rockford International Airport
    Mon, May 6Allegiant Air
    $81
    Find More Flights

Frequently Asked Questions

  • When are flight tickets from Orlando (ORL) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Orlando to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much do flights from Orlando (ORL) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around $225.
  • How long does it take to fly from Orlando (ORL) to Chicago (CHI) and what is the distance?

    It takes around 3 hours 50 minutes to fly from Orlando (ORL) to Chicago (CHI).
  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.
  • What are the most popular airlines that fly from Orlando (ORL) to Chicago (CHI)?

    Airlines with flights from Orlando (ORL) to Chicago (CHI): Volaris, Qatar Airways, Royal Jordanian, Azul Airlines, American Airlines, Spirit Airlines, Southwest Airlines and United Airlines.

Travel Info | Orlando to Chicago

Cheapest nonstop flight price

$19

Cheapest round-trip ticket price

$31

Off-season for travel

March

Peak season for travel

September