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Cheap flights from Orlando Airport to Chicago from $45

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 8/29. 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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Cheap round-trip flights

Frontier Logo
5:50 am - 7:44 amMCO-MDW
2h 54mnonstop
Frontier Logo
8:39 am - 12:20 pmMDW-MCO
2h 41mnonstop
$64Frontier
Find Deal
dom., oct. 12 - vie., oct. 17
Frontier Logo
8:00 am - 9:54 amMCO-MDW
2h 54mnonstop
Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
$68Frontier
Find Deal
sáb., ago. 30 - vie., sep. 5
Frontier Logo
8:00 am - 9:51 amMCO-MDW
2h 51mnonstop
Frontier Logo
8:19 am - 12:00 pmMDW-MCO
2h 41mnonstop
$78Frontier
Find Deal
sáb., sep. 13 - lun., sep. 15
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
Frontier Logo
10:13 am - 1:55 pmMDW-MCO
2h 42mnonstop
$79Frontier
Find Deal
vie., oct. 3 - dom., oct. 5
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
Frontier Logo
8:19 am - 12:00 pmMDW-MCO
2h 41mnonstop
$89Frontier
Find Deal
vie., sep. 12 - lun., sep. 15
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
Frontier Logo
10:13 am - 1:55 pmMDW-MCO
2h 42mnonstop
$91Frontier
Find Deal
vie., sep. 19 - dom., sep. 21
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
Frontier Logo
10:13 am - 1:55 pmMDW-MCO
2h 42mnonstop
$92Frontier
Find Deal
vie., sep. 19 - dom., sep. 21
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
Frontier Logo
10:51 am - 2:33 pmMDW-MCO
2h 42mnonstop
$99Frontier
Find Deal
vie., sep. 5 - sáb., sep. 6
Southwest Logo
7:15 am - 9:00 amMCO-MDW
2h 45mnonstop
Southwest Logo
8:05 pm - 11:40 pmMDW-MCO
2h 35mnonstop
$157Southwest
Find Deal
sáb., sep. 27 - mié., oct. 1
Southwest Logo
8:40 pm - 10:25 pmMCO-MDW
2h 45mnonstop
Southwest Logo
4:45 pm - 8:25 pmMDW-MCO
2h 40mnonstop
$158Southwest
Find Deal
jue., ago. 28 - mié., sep. 3

Frontier flights from Orlando Airport to Chicago Midway Airport

Our best Frontier deals on Orlando Airport to Chicago Midway Airport flight tickets
Frontier
Oct 12
MCO5:50 amOrlando
2h 54m
MDW7:44 amChicago Midway
Oct 17
MDW8:39 amChicago Midway
2h 41m
MCO12:20 pmOrlando
$64
Find similar
Frontier
Aug 30
MCO8:00 amOrlando
2h 54m
MDW9:54 amChicago Midway
Sep 5
MDW9:48 amChicago Midway
2h 40m
MCO1:28 pmOrlando
$68
Find similar
Frontier
Sep 13
MCO8:00 amOrlando
2h 51m
MDW9:51 amChicago Midway
Sep 15
MDW8:19 amChicago Midway
2h 41m
MCO12:00 pmOrlando
$78
Find similar

Southwest flights from Orlando Airport to Chicago Midway Airport

Our best Southwest deals on Orlando Airport to Chicago Midway Airport flight tickets
Southwest
Sep 27
MCO7:15 amOrlando
2h 45m
MDW9:00 amChicago Midway
Oct 1
MDW8:05 pmChicago Midway
2h 35m
MCO11:40 pmOrlando
$157
Find similar
Southwest
Aug 28
MCO8:40 pmOrlando
2h 45m
MDW10:25 pmChicago Midway
Sep 3
MDW4:45 pmChicago Midway
2h 40m
MCO8:25 pmOrlando
$158
Find similar
Southwest
Sep 18
MCO7:35 amOrlando
2h 45m
MDW9:20 amChicago Midway
Sep 21
MDW6:20 pmChicago Midway
2h 40m
MCO10:00 pmOrlando
$159
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Orlando Airport to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated julio 31, 2025.
Use the filters below to find and compare flights from Orlando Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

dom. 10/12

5:50 am-7:44 am

Nonstop2h 54m

Chicago Midway

vie. 10/17

8:39 am-12:20 pm

Nonstop2h 41m

$64

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

sáb. 8/30

8:00 am-9:54 am

Nonstop2h 54m

Chicago Midway

vie. 9/5

9:48 am-1:28 pm

Nonstop2h 40m

$68

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

sáb. 9/13

8:00 am-9:51 am

Nonstop2h 51m

Chicago Midway

lun. 9/15

8:19 am-12:00 pm

Nonstop2h 41m

$78

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

vie. 10/3

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

dom. 10/5

10:13 am-1:55 pm

Nonstop2h 42m

$79

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

vie. 9/12

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

lun. 9/15

8:19 am-12:00 pm

Nonstop2h 41m

$89

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

vie. 9/19

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

dom. 9/21

10:13 am-1:55 pm

Nonstop2h 42m

$91

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

vie. 9/19

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

dom. 9/21

10:13 am-1:55 pm

Nonstop2h 42m

$92

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

vie. 9/5

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

sáb. 9/6

10:51 am-2:33 pm

Nonstop2h 42m

$99

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

sáb. 9/27

7:15 am-9:00 am

Nonstop2h 45m

Chicago Midway

mié. 10/1

8:05 pm-11:40 pm

Nonstop2h 35m

$157

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

jue. 8/28

8:40 pm-10:25 pm

Nonstop2h 45m

Chicago Midway

mié. 9/3

4:45 pm-8:25 pm

Nonstop2h 40m

$158

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Orlando Airport to Chicago Midway Airport

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 cheapest month to fly to Chicago Midway Airport?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Orlando Airport, with most prices found around $87. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Orlando Airport during the month September is also very affordable. Most momondo users find prices during this month for around $167.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Orlando Airport. The lowest ticket price found for a Friday departure recently was $176. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Tuesday is the most expensive day to depart from Orlando Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $285.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Orlando Airport at noon is the least expensive time of day to depart. momondo users have found prices as low as $179 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $292. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Orlando to Chicago Midway flight route?

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

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Orlando Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $202 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Orlando Airport for as low as $170 on momondo.

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

There are 1 cabin classes available to choose from on Orlando to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Orlando Airport to Chicago Midway Airport flight prices changed over time?

As of July 2025, prices for Orlando Airport to Chicago Midway Airport flights are approximately 11% more expensive when compared to flights at the same time last year.

When to book flights from Orlando Airport to Chicago Midway Airport

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

Cheap Orlando Airport to Chicago Midway Airport (MCO to MDW) flight deals and tips

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

Best Price Found

$45

Fastest flight time

2h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Orlando Airport in the past 72 hours is $45. The best round-trip flight deal from Orlando Airport to Chicago Midway Airport found on momondo in the last 72 hours is $64.
The fastest flight from Orlando Airport to Chicago Midway Airport takes 2h 45m
Direct flights go from Orlando Airport to Chicago Midway Airport every day.
Search flight deals

  • How far is Orlando to Chicago Midway by plane?

    The distance between Orlando and Chicago Midway is about 990.5 mi. 2h 45m is a normal flight duration for this route.

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

    Prices for flights from Orlando Airport to Chicago Midway Airport were last updated today.

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

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

    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 Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Orlando Airport to Chicago Midway Airport?

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

Best airlines flying from Orlando Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Orlando Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $87Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
DeltaPriceFrom $114Free CancellationRating
8.0
7,981 reviews
Search Delta flights
SouthwestPriceFrom $166Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

  • Southwest Flights From Orlando Airport to Chicago Midway Airport

    The lowest priced Southwest flight from Orlando Airport to Chicago Midway Airport from the last 72 hours was $166. Generally, Southwest has 31 flights on this route every week with an average price of $339. Southwest is rated 8.0/10 by our users.

  • Frontier Flights From Orlando Airport to Chicago Midway Airport

    Frontier (5.9/10 from 3,239 reviews) operates around 2 flights from Orlando Airport to Chicago Midway Airport in any given week. The average Frontier airfare for this route is around $171, with deals from around $87 rare but found on momondo. Referenced prices are for round-trip Orlando Airport to Chicago Midway Airport flight searches in the last 72 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Orlando to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

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

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

Once you have performed a search for Orlando to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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.

An easier way to manage your Chicago Midway Airport trip

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