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Latest Flight Deals from Orlando to Chicago

Book one-way or return flights from Orlando to Chicago from as little as €21. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • MCO22:59
        3h
        Direct
        ORD00:59
        Wed, Aug 21|Orlando - Chicago|Frontier Airlines
        €21€39
        45% OFF
        45% OFF
        €39€21
      • MCO12:11
        2h 48m
        Direct
        MDW13:59
        Thu, Sep 12|Orlando - Chicago|Frontier Airlines
        €25€39
        36% OFF
        36% OFF
        €39€25
      • MCO22:57
        3h 2m
        Direct
        ORD00:59
        Wed, Jul 10|Orlando - Chicago|Frontier Airlines
        €25€39
        35% OFF
        35% OFF
        €39€25
      • MCO05:06
        3h 2m
        Direct
        ORD07:08
        Tue, Jul 2|Orlando - Chicago|Frontier Airlines
        €26
        €26
      • MCO09:00
        2h 48m
        Direct
        MDW10:48
        Mon, Sep 16|Orlando - Chicago|Frontier Airlines
        €30
        €30
      • MCO22:59
        3h
        Direct
        ORD00:59
        Thu, Aug 29|Orlando - Chicago|Frontier Airlines
        €31
        €31
      • MCO22:59
        3h
        Direct
        ORD00:59
        Thu, Aug 8|Orlando - Chicago|Frontier Airlines
        €31
        €31
      • MCO22:59
        3h
        Direct
        ORD00:59
        Wed, Aug 7|Orlando - Chicago|Frontier Airlines
        €32
        €32
      • MCO22:59
        3h
        Direct
        ORD00:59
        Tue, Aug 20|Orlando - Chicago|Frontier Airlines
        €33
        €33
      • MCO22:27
        3h 2m
        Direct
        ORD00:29
        Tue, Jul 16|Orlando - Chicago|Frontier Airlines
        €34
        €34
      • ORL13:00
        3h 5m
        Direct
        CHI14:00
        Mon, Jul 8|Orlando - Chicago|Frontier Airlines
        Find More Flights
        Find More Flights

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

Searching for the best last minute flight from Orlando to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Orlando to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Orlando to Chicago

View airlines operating 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 €21
Spirit Airlines
From €36
American Airlines
From €58
United Airlines
From €73
Sun Country Airlines
From €81
Delta Air Lines
From €82
Allegiant Air
From €82
Southwest Airlines
From €94
Jetblue Airways
From €99
Silver Airways
From €130
ANA airlines

Find more flights and airlines

Alternative Routes from Orlando to Chicago

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Orlando to Chicago.

  • Cheapest
    Frontier Airlines
    MCO
    22:59
    3h 0m
    Direct
    ORD
    00:59
    Orlando International Airport - O'Hare International Airport
    Wed, Aug 21Frontier Airlines
    €21
  • Frontier Airlines
    MCO
    12:11
    2h 48m
    Direct
    MDW
    13:59
    Orlando International Airport - Midway International Airport
    Thu, Sep 12Frontier Airlines
    €25
  • Allegiant Air
    SFB
    14:58
    2h 41m
    Direct
    RFD
    16:39
    Orlando Sanford International Airport - Chicago Rockford International Airport
    Wed, Jul 17Allegiant Air
    €82
  • Allegiant Air
    SFB
    14:58
    2h 41m
    Direct
    RFD
    16:39
    Orlando Sanford International Airport - Chicago Rockford International Airport
    Wed, Jul 17Allegiant Air
    €82
    Find More Flights

How do I find the cheapest flights?

  • 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 €203.

  • How long does it take to fly from Orlando (ORL) to Chicago (CHI) and what is the distance?

    It takes around 3 hours 36 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, Southwest Airlines and Frontier Airlines.

How to find a cheap flight from Orlando to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Orlando to Chicago. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com
Flight Information from Orlando to Chicago

Cheapest nonstop flight price

€21

Cheapest round-trip ticket price

€45

Off-season for travel

April

Peak season for travel

December

Flight distance

1,588.53km

Average flight time

3 hours 36 minutes

Popular airline

American Airlines

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