Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Orlando from $38

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Orlando departing on 7/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.

Find the cheapest flights from Chicago to Orlando

Cheap round-trip flights

Allegiant Air Logo
8:04 pm - 11:39 pmRFD-SFB
2h 35mnonstop
Allegiant Air Logo
6:30 am - 8:12 amSFB-RFD
2h 42mnonstop
$75Allegiant Air
Find Deal
Fri, Jul 11 - Sat, Jul 19
Allegiant Air Logo
9:02 am - 12:39 pmRFD-SFB
2h 37mnonstop
Allegiant Air Logo
6:30 am - 8:12 amSFB-RFD
2h 42mnonstop
$76Allegiant Air
Find Deal
Sat, Jul 5 - Sat, Jul 12
Allegiant Air Logo
8:04 pm - 11:39 pmRFD-SFB
2h 35mnonstop
Allegiant Air Logo
8:30 am - 10:12 amSFB-RFD
2h 42mnonstop
$82Allegiant Air
Find Deal
Fri, Jul 4 - Wed, Jul 9
Spirit Airlines Logo
10:46 am - 2:30 pmORD-MCO
2h 44mnonstop
Spirit Airlines Logo
6:15 pm - 8:23 pmMCO-ORD
3h 08mnonstop
$98Spirit Airlines
Find Deal
Fri, Jun 13 - Tue, Jun 17
Frontier Logo
5:03 pm - 9:04 pmORD-MCO
3h 01mnonstop
Frontier Logo
8:00 am - 10:17 amMCO-ORD
3h 17mnonstop
$99Frontier
Find Deal
Wed, Jun 11 - Wed, Jun 18
Spirit Airlines Logo
7:49 pm - 11:37 pmORD-MCO
2h 48mnonstop
Spirit Airlines Logo
3:08 pm - 5:17 pmMCO-ORD
3h 09mnonstop
$100Spirit Airlines
Find Deal
Tue, Jul 8 - Fri, Jul 11
Frontier Logo
4:26 pm - 8:28 pmORD-MCO
3h 02mnonstop
Frontier Logo
8:00 am - 10:14 amMCO-ORD
3h 14mnonstop
$102Frontier
Find Deal
Fri, Jul 11 - Wed, Jul 16
American Airlines Logo
6:44 pm - 10:40 pmORD-MCO
2h 56mnonstop
American Airlines Logo
8:37 am - 10:41 amMCO-ORD
3h 04mnonstop
$175American Airlines
Find Deal
Sat, Jul 19 - Wed, Jul 23
United Airlines Logo
6:00 am - 9:47 amORD-MCO
2h 47mnonstop
United Airlines Logo
9:32 am - 11:39 amMCO-ORD
3h 07mnonstop
$239United Airlines
Find Deal
Mon, Jun 23 - Wed, Jun 25
United Airlines Logo
6:00 am - 9:48 amORD-MCO
2h 48mnonstop
United Airlines Logo
11:00 am - 1:07 pmMCO-ORD
3h 07mnonstop
$243United Airlines
Find Deal
Sun, Jun 22 - Wed, Jul 2

Southwest flights from Chicago to Orlando

Our best Southwest deals on Chicago to Orlando flight tickets
Southwest
Jul 8
MDW5:20 pmChicago Midway
2h 45m
MCO9:05 pmOrlando
Jul 15
MCO6:20 amOrlando
2h 50m
MDW8:10 amChicago Midway
Southwest
Jul 8
ORD4:00 pmChicago O'Hare Intl
15h 30m
1 stop
MCO8:30 amOrlando
Jul 11
MCO3:45 pmOrlando
3h 10m
ORD5:55 pmChicago O'Hare Intl
Southwest
May 27
MDW7:55 pmChicago Midway
2h 35m
MCO11:30 pmOrlando
Jun 3
MCO5:30 pmOrlando
5h 20m
1 stop
MDW9:50 pmChicago Midway

Frontier flights from Chicago to Orlando

Our best Frontier deals on Chicago to Orlando flight tickets
Frontier
Jun 11
ORD5:03 pmChicago O'Hare Intl
3h 01m
MCO9:04 pmOrlando
Jun 18
MCO8:00 amOrlando
3h 17m
ORD10:17 amChicago O'Hare Intl
Frontier
Jul 11
ORD4:26 pmChicago O'Hare Intl
3h 02m
MCO8:28 pmOrlando
Jul 16
MCO8:00 amOrlando
3h 14m
ORD10:14 amChicago O'Hare Intl
Frontier
Jun 9
ORD5:08 pmChicago O'Hare Intl
3h 01m
MCO9:09 pmOrlando
Jun 11
MCO9:57 pmOrlando
3h 13m
ORD12:10 amChicago O'Hare Intl

See travel insights to Orlando from

How to get the cheapest flight ticket from Chicago to Orlando

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 Chicago and Orlando?

What is the cheapest month to fly to Orlando?

The month of September is, on average, the cheapest month to fly to Orlando from Chicago, with most prices found around $184. If you’re not able to fly to Orlando in September, then August is your next best option. Flight prices from Chicago to Orlando during August average around $194.

What is the cheapest day to depart on your flight to Orlando?

Our data shows that Tuesday is the least expensive day to fly to Orlando. Tickets to fly out on this day can be as low as $266. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $314.

What is the cheapest time of day to depart on your flight to Orlando?

The cheapest time of day to fly to Orlando is in the afternoon when flights can be purchased for as low as $241. In contrast, the most expensive time of day to depart to Orlando is in the morning when prices are around $308.

What is the cheapest Chicago to Orlando flight route?

Fly from Chicago Midway to Orlando for the best Chicago - Orlando flight prices

How far in advance should I book a flight to Orlando?

You are more likely to see cheaper flights to Orlando from Chicago when booking 4 weeks ahead of your departure date. In general, you can expect to find flights to Orlando for around $294 when searching 4 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Orlando from Chicago for as low as $240 on momondo.

What cabin class options are available on Chicago to Orlando flights?

There are 4 cabin classes available to choose from on Chicago to Orlando flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Orlando flight prices changed over time?

As of May 2025, prices for Chicago to Orlando flights are approximately 6% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Orlando

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Orlando according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Orlando (CHI to ORL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Orlando

Best Price Found

$38

Fastest flight time

2h 30m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun

Airports in Orlando

2 airports
The best one-way flight to Orlando from Chicago in the past 72 hours is $38. The best round-trip flight deal from Chicago to Orlando found on momondo in the last 72 hours is $75.
The fastest flight from Chicago to Orlando takes 2h 30m
Direct flights go from Chicago to Orlando on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: Southwest and Allegiant Air.
There are 2 airports near Orlando: Orlando (MCO), Orlando Sanford Intl (SFB)

  • How far is Chicago to Orlando by plane?

    The straight-line distance from Chicago to Orlando is 985.3 mi. A reasonable flight in good conditions will take 2h 30m.

  • When did momondo last update prices for flights from Chicago to Orlando?

    Prices for flights from Chicago to Orlando refresh daily.

  • How many operators does momondo search for flights from Chicago to Orlando?

  • How old do you have to be to fly from Chicago to Orlando?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Orlando.

  • What documentation or ID do you need to fly to Orlando?

    The travel and health documents required for your trip to Orlando 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 Orlando. 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 Chicago to Orlando?

  • What is the most popular airline from Chicago to Orlando?


Best airlines flying from Chicago to Orlando

Compare and see reviews for airlines that fly from Chicago to Orlando with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $72Free CancellationRating
6.0
3,288 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $88Free CancellationRating
6.3
8,004 reviews
Search Spirit Airlines flights
Allegiant AirPriceFrom $119Free CancellationRating
7.3
733 reviews
Search Allegiant Air flights
American AirlinesPriceFrom $179Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $193Free CancellationRating
7.4
8,745 reviews
Search United Airlines flights
DeltaPriceFrom $196Free CancellationRating
8.0
7,950 reviews
Search Delta flights
SouthwestPriceFrom $217Free CancellationRating
8.0
4,291 reviews
Search Southwest flights
  • Southwest Flights From Chicago to Orlando

    Southwest flight deals from Chicago to Orlando start from $217 round-trip. Over the 57 Southwest flights for this route in a normal week, average airfare is usually $396 round-trip - but some users have found much cheaper deals with momondo.

  • United Airlines Flights From Chicago to Orlando

    United Airlines (7.4/10 from 8,745 reviews) operates around 23 flights from Chicago to Orlando in any given week. The average United Airlines airfare for this route is around $364, with deals from around $193 rare but found on momondo. Referenced prices are for round-trip Chicago to Orlando flight searches in the last 72 hours.


Traveling to a place near Orlando?

Book flights to Orlando if you plan to visit one of these locations
Bay Lake

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Orlando?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Orlando. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Orlando with flexible booking policies on momondo?

Yes. All flights to Orlando from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Orlando?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Orlando from Chicago.

I’m not ready to book a flight from Chicago to Orlando right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Orlando from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


An easier way to manage your Orlando trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 5/27
Tue 6/3

Find better results for your trip to the United States

Fly into one of these airports located in Orlando

Airports listed have a maximum distance of 18.3 mi from Orlando