• Flights
  • Packages
  • Hotels
  • Cars
Round-trip
Coach

Refine your search by airline, by city or airport or direct flights

Bundle & Save

Your trip. Designed by our 24/7 travel experts

Enjoy personalized planning with real human support. Call Our Travel Experts 24/7. Call 1-646-738-4832 1-646-738-4832 and say DIAL10 to save.

Expires Jun 30, 2026. Where applicable discount applies to service fees for qualified airline tickets. Amount of service fee discount varies: maximum savings of $10 per person applied to bookings from one (1) traveler up to five (5) travelers; the maximum discount applied is $50. Promo Code and Instant Savings offers can be combined up to the amount of our service fees but cannot be used or combined with any other coupons, promotions or special offers. May be withdrawn at any time without notice. Promo code only applicable for bookings created over the phone through our call center.

What travelers love about OneTravel

20+ Years of ExperienceHelping 40M+ travelers worldwide Partnered with 1M+ verified hotels

24/7 Travel AdvisorsPersonalized planning and real human support, anytime

Upfront PricingOur prices include taxes and fees

Members Save MoreJoin ClubMiles rewards program and save on every booking

Round TripOne Way

What our customers say about our service?

Submit a review
  • Decent experienceMy experience with OneTravel was decent but could use some improvements. I found a good deal, but na vigating the site was a bit tricky at times. Thank....

    Read more

    Daniel Brown · Apr 22, 2026
  • Smooth Customer ServiceIt was a great experience using OneTravel to book my honeymoon trip to Bali. The customer service was outstanding, and they helped me with the best options for our budget. I appreciated their travel advice, and everything went smoothly. Would highly recommend!

    Read more

    Sophia Martinez · Apr 22, 2026
  • Prices are excellentI had a good experience with OneTravel, although there were a few hiccups during the booking process. Customer service was helpful in resolving my issues. The prices were excellent, and I found a great last-minute deal. The confirmation emails were timely, and I loved the easy access to my itinerary online.

    Read more

    Benjamin Roberts · Apr 22, 2026
  • A solid choiceI had a good experience with OneTravel while booking my family vacation. The price was right, and we could get seated together. The only issue I faced was with the payment processing, but their support team was quick to assist. Overall, a solid choice for travel planning.

    Read more

    Michael Harris · Apr 22, 2026

Orlando to Chicago Flight Route Information

Travel Distance:992 Miles
Airlines Flying This Route: Spirit Airlines, American Airlines, Frontier Airlines
Weekly Flights:2
Avg. Flight Duration:3.0 Hours

Insights About Flying from Orlando to Chicago

Q. Which is the high season to travel from Orlando to Chicago?
Ans. The month of February is considered the high season for flying from ORL to CHI. Traveling during the high season can affect ticket prices and availability, making this data crucial for trip planning.
Q. How many direct flights are available from ORL to CHI?

A. There are a total of 1407 direct flights from Orlando to Chicago. For travelers seeking convenience and shorter travel times, this data is important when choosing flight options.

Q. Which is the low season to travel from Orlando to Chicago?

A. August, March, November is considered the low season for traveling from Orlando to Chicago, Illinois. Travelers looking for cost-effective options and fewer crowds may consider traveling during this period.

Q. How many daily flights are there between Orlando to Chicago?

A. There are as many as 47 daily flights available for travelers between ORL to CHI. This data offers flexibility in choosing departure times that best suit your schedule.

Q. At what time does the last flight depart to Chicago?

A. The last flight to Chicago typically departs between 10:00PM - 11:00PM. Travelers who prefer late-night departures will find this information valuable for planning their journey.

Q. What percentage of travelers spent an average of 3 days in Chicago, Illinois?

A. Approximately 34.12% of travelers spent an average of 3 days exploring Chicago. This information can assist in planning the duration of your stay in Chicago

Q. What percentage of ORL to CHI flyers traveled with kids under 14?

A. About 11% of passengers on flights from Orlando to Chicago were accompanied by children under the age of 14. This information is useful if you're planning a family trip and want to know how common it is to travel with young children on this route.

Q. What percentage of Orlando to Chicago travelers were over 60 years old?

A. A notable 12% of travelers were aged 60 or older. This statistic provides insights for senior travelers or those seeking a mature travel demographic.

Q. What percentage of ORL to CHI travelers were millennials?

A. Millennials make up a significant portion of travelers on this route, accounting for 34% of all passengers. If you're a millennial looking to connect with like-minded travelers, this statistic might interest you.

Q. What percentage of Orlando to Chicago travelers were female?

A. Almost half of the passengers, approximately 52% were female. Knowing the gender distribution can be useful for solo female travelers or those interested in gender-related travel insights.

Q. What percent of Orlando to Chicago travellers booked first or business class?

A. 9% of travelers booked first or business class on this route.

Q. At what time the earliest flight departs from Orlando?

A. The earliest flight departs at 7:00AM - 8:00AM.

Q. Which is the most popular airport for connecting flights between Orlando to Chicago?

A. Sarasota-Bradenton International Airport is the most popular airport for connecting flights between ORL to CHI.

Q. On which days one can have the most flight options in Chicago?

A. Monday offer the most flight options in Chicago.

§ All flight facts are based on last 3 months' data except the highest and lowest booking months that are based on last 3 months' data.
Recent posts View all posts
Travel Easy India: Your Guide to a Stress-Free Journey
Read more
Travel Easy China: Your Guide to a Stress-Free Trip
Read more
Travel Easy Vietnam: Your Guide to a Stress-Free Trip
Read more
Travel Easy Philippines: Your Guide to a Stress-Free Trip  
Read more
Global Greens: Top Destinations for Vegetarian Travelers
Read more
View all posts

Cheap Flights from Orlando to Chicago

Book your flights from Orlando to Chicago and on airfares. Decorated with miles of beautiful beaches, world class museums and amazing parks, city of Chicago would certainly spoil you for choices. Third most populous city in United States, Chicago certainly deserves a place on your travel itinerary. Spend a romantic evening with your loved one at North Avenue Beach and explore more than 30,000 marine species at the famous Shedd Aquarium. Don’t forget to pamper yourself with the best of brands and cuisines at the Magnificent Mile. United Airlines, US Airways, American Airlines and JetBlue Airways are some of the major airlines that offer flights from Orlando to Chicago. It takes about three hours and forty five minutes excluding the layover time to cover the destined 987 miles on flights from Orlando to Chicago and although there are plenty of entertainment options provided by the carriers, it’s always a good idea to carry a nice book with you.