Cheap flights from Orlando Airport to Chicago from $110
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Orlando Airport to Chicago departing on 10/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Our best Frontier deals on Orlando Airport to Chicago flight tickets
JetBlue flights from Orlando Airport to Chicago
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Fly from
Fly to
Route
Depart
Return
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Tue 10/27
7:04 am-12:51 pm
1 stop6h 47m
Chicago O'Hare Intl
Sat 10/31
7:15 am-5:24 pm
1 stop9h 09m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Tue 10/27
7:04 am-12:51 pm
1 stop6h 47m
Chicago O'Hare Intl
Tue 10/27
7:50 pm-8:10 am
1 stop11h 20m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Mon 11/23
9:00 am-1:32 pm
1 stop5h 32m
Chicago O'Hare Intl
Fri 11/27
2:59 pm-10:19 pm
1 stop6h 20m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Fri 12/11
6:50 pm-11:33 pm
1 stop5h 43m
Chicago O'Hare Intl
Wed 12/16
2:59 pm-10:08 pm
1 stop6h 09m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Tue 11/3
9:22 am-11:29 am
Nonstop3h 07m
Chicago O'Hare Intl
Tue 11/3
5:45 pm-9:37 pm
Nonstop2h 52m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Wed 12/2
9:09 am-11:17 am
Nonstop3h 08m
Chicago O'Hare Intl
Wed 12/2
4:15 pm-8:05 pm
Nonstop2h 50m
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Thu 12/3
9:25 am-11:20 am
Nonstop2h 55m
Chicago Midway
Sat 12/5
6:30 pm-10:10 pm
Nonstop2h 40m
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Tue 10/27
6:35 am-8:25 am
Nonstop2h 50m
Chicago Midway
Wed 10/28
3:25 pm-7:00 pm
Nonstop2h 35m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Thu 11/5
5:26 pm-7:50 pm
Nonstop3h 24m
Chicago O'Hare Intl
Mon 11/9
4:05 pm-7:56 pm
Nonstop2h 51m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Thu 12/10
5:26 pm-7:50 pm
Nonstop3h 24m
Chicago O'Hare Intl
Wed 12/16
12:41 pm-4:33 pm
Nonstop2h 52m
See travel insights to Chicago from
How to get the cheapest flight ticket from Orlando Airport to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Orlando Airport and Chicago?
Prices are currently typical for flights on this route.
Typical prices usually range from $178 to $384.The lowest price recently found on this route was $192.
What is the cheapest month to fly to Chicago?
The month of January is, on average, the cheapest month to fly to Chicago from Orlando Airport, with most prices found around $169. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Orlando Airport to Chicago during February average around $176.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $334. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Orlando Airport to Chicago for around $542.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Orlando Airport to Chicago during this time can be as low as $257. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $572.
What is the cheapest Orlando to Chicago flight route?
Fly from Orlando to Chicago Midway for the best Orlando - Chicago flight prices
How far in advance should I book a flight from Orlando Airport to Chicago?
You are more likely to see cheaper flights to Chicago from Orlando Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $260 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando Airport for as low as $227 on momondo.
What cabin class options are available on Orlando Airport to Chicago flights?
There are 4 cabin classes available to choose from on Orlando Airport to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Orlando Airport to Chicago flights?
You could potentially save up to 9% on your flight if you consider stops on a Orlando Airport to Chicago flight.
How have Orlando Airport to Chicago flight prices changed over time?
As of October 2026, prices for Orlando Airport to Chicago flights are approximately 12% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Orlando to Chicago?
JetBlue, United Airlines, and Southwest are the most popular carriers operating from Orlando to Chicago
What airlines fly to Chicago?
Frontier, American Airlines and United Airlines are the top three most popular airlines that fly to Chicago from Orlando Airport according to our data. Frontier is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How often are flights from Orlando to Chicago delayed?
Historically, on average around 18% of flights between Orlando and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 144 minutes.
What is the most punctual flight time for Orlando to Chicago flights?
Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.
What day of the week experiences the fewest flight delays on this route?
Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.
Which airline has the best punctuality record on Orlando to Chicago flights?
According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.
How many flights depart from Orlando Airport to Chicago on average per day?
65 flights are operational daily from Orlando Airport to Chicago as of October 2026. The most popular departure time for this route is 2:00PM, with 46% of flights per day taking off in the afternoon.
How many flights depart from Orlando Airport to Chicago on average per week?
458 flights are operational weekly from Orlando Airport to Chicago as of October 2026. The most popular departure day for this route is Wed, with 16% of flights per week taking off on this day.
When to book flights from Orlando Airport to Chicago
Cheap Orlando Airport to Chicago (MCO to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Orlando Airport to Chicago
Frequently asked questions about flying from Orlando Airport to Chicago
How far is Orlando to Chicago by plane?
There are 993.7 mi between Orlando and Chicago. A reasonable flight in good conditions will take 2h 50m.
When did momondo last update prices for flights from Orlando Airport to Chicago?
Prices for flights from Orlando Airport to Chicago refresh daily.
How many operators does momondo search for flights from Orlando Airport to Chicago?
As of October 2026, there are 4 operators available to choose from for flights from Orlando Airport to Chicago.
How old do you have to be to fly from Orlando Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Orlando Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Orlando Airport to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Orlando Airport to Chicago is Airbus A321neo (21.11% of total bookings). The next most popular plane models are Boeing 737-800 (12.03%), Airbus A321-100/200 (11.52%), and Boeing 737 MAX 8 (8.52%).
What is the most popular airline from Orlando Airport to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Orlando Airport to Chicago is Frontier (48% of total bookings). The next most popular airlines are United Airlines (19%), Southwest (17%), and American Airlines (14%).
Best airlines flying from Orlando Airport to Chicago
Compare and see reviews for airlines that fly from Orlando Airport to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $68 | Free Cancellation | Rating 5.6 2,551 reviews | |||
| PriceFrom $155 | Free Cancellation | Rating 7.9 4,224 reviews | |||
| PriceFrom $161 | Free Cancellation | Rating 7.4 10,322 reviews | |||
| PriceFrom $174 | Free Cancellation | Rating 7.0 12,146 reviews |
Southwest Flights From Orlando Airport to Chicago
Across 53 Southwest flights from Orlando Airport to Chicago this week, the average price was $344, with the best Southwest deals starting from $155 round-trip. 4,224 users have rated Southwest on momondo, with an average score of 7.9/10.
United Airlines Flights From Orlando Airport to Chicago
Another popular option for Orlando Airport to Chicago flights is United Airlines (7.4/10, 10,322 ratings). United Airlines flies from Orlando Airport to Chicago around 53 times per week, with deals starting from $161 round-trip and rising to an average price of around $352.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Orlando to Chicago?
Finding the right flight to Chicago from Orlando is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Orlando to Chicago with flexible booking policies on momondo?
All flight searches from Orlando to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Orlando to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Orlando. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Orlando to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Orlando are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.