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Cheap Flights from Orlando (ORL) to Chicago (CHI)

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Orlando to Chicago Flights

F9

Ohare International

17:03

Chicago

24 May 2025
2h 57m

21:57

Orlando

08 Jun 2025
$119.67
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NK

Ohare International

07:47

Chicago

24 May 2025
2h 39m

21:25

Orlando

08 Jun 2025
$136.49
Book Now
UA

Ohare International

06:00

Chicago

25 May 2025
2h 47m

07:30

Orlando

09 Jun 2025
$291.87
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AA

Ohare International

07:10

Chicago

26 May 2025
2h 40m

08:41

Orlando

10 Jun 2025
$301.32
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DL

Ohare International

05:30

Chicago

25 May 2025
4h 11m

06:15

Orlando

09 Jun 2025
$307.40
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B6

Ohare International

06:15

Chicago

25 May 2025
6h 24m

14:20

Orlando

09 Jun 2025
$318.59
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The displayed flights from Orlando to Chicago are round-trip. Airfares are non-warranted and subject to change. The fares comprise base fare, fuel surcharges, airline/airport taxes, and our service fee.

Search, Compare and Book Flights from Orlando to Chicago

Cheapfaremart takes away the hassles of fare comparison and flight booking from your travel planning. We list fares from ORL to CHI with all the carriers operating on the route. We have invested in the best of travel technology that pulls out the top Chicago airfare deals available with different passenger carriers.

Cheapfaremart is the leading online travel agency approved by the American Society of Travel Agents. We help you find flights by your convenience — search flights by departure or arrival timing or by airlines. So, travel in the time that suits you, and also don’t miss the miles or rewards offered by your favorite travel suppliers.

If you are traveling in a group with size 10 or more, you deserve an additional flight discount. We help corporates, academic, and other institutions to save big on their group flight booking.

Season Brings a Major Fluctuation in Ticket Pricing

High

  • “Summer”

  • Month-wise: June, July August

Low

  • “Early spring and fall”

  • Month-wise: March, November

Shoulder

  • “Spring, autumn”

  • Month-wise: April, May, Sep, October

Worst

  • “Winter”

  • Month-wise: December, January, February

Airport in Orlando Handling Departure Flights to Chicago

1. Orlando International Airport

Airport Code: MCO

Location: Six miles (10 km) southeast of Downtown Orlando

Airlines operating nonstop flights to Chicago: Spirit, United, American, Frontier

Airlines operating connecting flights to Chicago: American, Spirit, Frontier, Delta, United

2. Daytona Beach International Airport

Airport Code: DAB

Location: 53 miles/85 km from Orlando, FL.

Airlines operating nonstop flights to Chicago: No Airlines

Airlines operating connecting flights to Chicago: American Airlines, Jetblue Airways, and United Airlines.

Arrival Airport Choices in Chicago

1. O’Hare International Airport

Airport Code: ORD

Location: 14 miles (23 km) northwest of the Loop business district

2. Chicago Midway International Airport

Airport Code: MDW

Location: Eight miles (13 km) from the Loop.

Number of Orlando to Chicago Flights per Day

MCO to ORD

Nonstop: 23

Duration: 03 hours 07 minutes

Airlines (Nonstop): Spirit, American, Frontier, United

Connecting: Over 750

Airlines (Connecting): American, Delta, United

Duration (Min): 04 hours 17 minutes to 18 hours (depending upon layover or transfer time)

MCO to MDW

Nonstop: 0

Connecting: 200

Airlines: Delta, Spirit, Frontier, American

Duration: From 04 hours 37 minutes to 12 hours

DAB to ORD

Nonstop: 0

Connecting flights: Yes

Number of flights per day: 391 (approx.)

Airlines: American, Delta

Duration: 4 hours 25 minutes to 18 hours (depending upon layover or transfer time)

How Long is the Flight from Orlando to Chicago?

The flight time from Orlando to Chicago is 2 hours 21 minutes (approximate). The flight distance between ORL and CHI is 985 miles/1584 km. Take note of the time difference between Chicago and Orlando. Chicago is one hour behind Orlando. You may observe some variation in flight time and distance based on the departure and arrival airport pair.

Departure-Arrival Airport

Flight Distance

Flight Time

MCO to ORD

2,215 miles/3564 km

4 hours 56 minutes

DAB to MDW

2,215 miles/3565 km

4 hours 56 minutes

MCO to MDW

2,171 miles/3494 km

4 hours 51 minutes

DAB to ORD

2,187 miles/3519 km

4 hours 52 minutes

Note: The flight distance and flight time are tentative. You should check with your airlines to have the precise information.

How to Book Cheap Flights from Orlando to Chicago?

Practice these simple flight booking hacks to discover cheap flight deals on Chicago flight booking.

1. Be flexible with your date

If you are flexible, you are likely to find the top ORL to Chicago flight deals. Scheduling your flight departure day on a Wednesday or Thursday, you can have the edge over the competition of getting a flight ticket that happens on the weekend.

2. Be flexible with your time

Majority of travelers travel in day hours. Going against the trend, if you opt for a red-eye flight, you have chances to save some cash.

3. Wait for the right season

The best time for getting good deals on flights is winter, especially in January and February. Late November and early December also see dips in pricing for flights. If you are heading in winter, you must add some extra layer as the nights see sub-zero temperature.

4. Don’t wait for unexpected fare drop

Patience pays off. However, it should not stop you from rationale decision-making when you come across any ORL to CHI fare which you understand is far below the average.

Confirm your one-way or round trip flight tickets from Orlando to Chicago now. You may get in touch with us over the phone or chat to see on-demand help in flight booking.

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“Terms and Conditions”

Discounts and savings on airfares are calculated based on several factors, including comparison of fares across more than 500 airlines. The quoted pricing reflects our best available fare at the time of search. Coupon codes are valid for applicable discounts on our service fees for eligible bookings. Additional terms may apply to specific offers, which will be disclosed at the time of booking.

Fare Disclosures

  • Unless otherwise specified, all listed fares are for round-trip travel and include applicable fuel surcharges, taxes, fees, and our service fees.

  • Displayed fares are based on historical pricing data and are subject to change.

  • Tickets are nonrefundable, nontransferable, name changes are not permitted, and subject to airline’s fare rules and restrictions.

  • Availability of the quoted fare is more likely on travel dates that fall on Tuesdays, Wednesdays, and Thursdays.

  • These fares may also require an advance purchase of up to 21 days and/or a Saturday night stay.

  • Blackout dates may apply, especially during peak travel periods or holidays. Travel on weekends or holidays may be subject to additional surcharges.

For further details, please review our full Terms and Conditions.

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