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Cheap flights from Orlando to Chicago from $43

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 to Chicago departing on 9/14. 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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0 bags

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Cheap round-trip flights

Frontier Logo
2:26 pm - 4:20 pmMCO-MDW
2h 54mnonstop
Frontier Logo
5:28 pm - 9:10 pmMDW-MCO
2h 42mnonstop
$63Frontier
Find Deal
Fri, Oct 10 - Mon, Oct 13
Frontier Logo
5:50 am - 7:44 amMCO-MDW
2h 54mnonstop
Frontier Logo
8:39 am - 12:20 pmMDW-MCO
2h 41mnonstop
$73Frontier
Find Deal
Fri, Oct 31 - Mon, Nov 3
Frontier Logo
1:16 pm - 3:11 pmMCO-MDW
2h 55mnonstop
Frontier Logo
11:31 am - 3:11 pmMDW-MCO
2h 40mnonstop
$78Frontier
Find Deal
Sat, Oct 11 - Sat, Oct 18
Frontier Logo
8:00 am - 9:51 amMCO-MDW
2h 51mnonstop
Frontier Logo
10:51 am - 2:33 pmMDW-MCO
2h 42mnonstop
$81Frontier
Find Deal
Sat, Sep 13 - Sat, Sep 20
Frontier Logo
8:00 am - 9:51 amMCO-MDW
2h 51mnonstop
Frontier Logo
8:19 am - 12:00 pmMDW-MCO
2h 41mnonstop
$82Frontier
Find Deal
Sat, Sep 13 - Mon, Sep 15
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
Frontier Logo
10:13 am - 1:55 pmMDW-MCO
2h 42mnonstop
$83Frontier
Find Deal
Fri, Sep 12 - Sun, Sep 14
Frontier Logo
8:00 am - 9:51 amMCO-MDW
2h 51mnonstop
Frontier Logo
8:19 am - 12:00 pmMDW-MCO
2h 41mnonstop
$84Frontier
Find Deal
Sat, Sep 20 - Mon, Sep 22
Frontier Logo
2:26 pm - 4:20 pmMCO-MDW
2h 54mnonstop
Frontier Logo
11:31 am - 3:11 pmMDW-MCO
2h 40mnonstop
$87Frontier
Find Deal
Fri, Oct 17 - Sat, Oct 25
Logo
6:32 pm - 11:17 pmMCO-MDW
5h 45m1 stop
Logo
10:13 am - 1:55 pmMDW-MCO
2h 42mnonstop
$134
Find Deal
Sat, Sep 20 - Sun, Sep 21
Logo
6:31 am - 3:58 pmMCO-MDW
10h 27m2 stops
Logo
10:51 am - 2:33 pmMDW-MCO
2h 42mnonstop
$141
Find Deal
Wed, Sep 17 - Sat, Sep 20

Frontier flights from Orlando to Chicago Midway Airport

Our best Frontier deals on Orlando to Chicago Midway Airport flight tickets
Frontier
Oct 10
MCO2:26 pmOrlando
2h 54m
MDW4:20 pmChicago Midway
Oct 13
MDW5:28 pmChicago Midway
2h 42m
MCO9:10 pmOrlando
$63
Find similar
Frontier
Oct 31
MCO5:50 amOrlando
2h 54m
MDW7:44 amChicago Midway
Nov 3
MDW8:39 amChicago Midway
2h 41m
MCO12:20 pmOrlando
$73
Find similar
Frontier
Oct 11
MCO1:16 pmOrlando
2h 55m
MDW3:11 pmChicago Midway
Oct 18
MDW11:31 amChicago Midway
2h 40m
MCO3:11 pmOrlando
$78
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Orlando 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 August 17, 2025.
Use the filters below to find and compare flights from Orlando to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 10/10

2:26 pm-4:20 pm

Nonstop2h 54m

Chicago Midway

Mon 10/13

5:28 pm-9:10 pm

Nonstop2h 42m

$63

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 10/31

5:50 am-7:44 am

Nonstop2h 54m

Chicago Midway

Mon 11/3

8:39 am-12:20 pm

Nonstop2h 41m

$73

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 10/11

1:16 pm-3:11 pm

Nonstop2h 55m

Chicago Midway

Sat 10/18

11:31 am-3:11 pm

Nonstop2h 40m

$78

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 9/13

8:00 am-9:51 am

Nonstop2h 51m

Chicago Midway

Sat 9/20

10:51 am-2:33 pm

Nonstop2h 42m

$81

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 9/13

8:00 am-9:51 am

Nonstop2h 51m

Chicago Midway

Mon 9/15

8:19 am-12:00 pm

Nonstop2h 41m

$82

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 9/12

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

Sun 9/14

10:13 am-1:55 pm

Nonstop2h 42m

$83

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 9/20

8:00 am-9:51 am

Nonstop2h 51m

Chicago Midway

Mon 9/22

8:19 am-12:00 pm

Nonstop2h 41m

$84

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 10/17

2:26 pm-4:20 pm

Nonstop2h 54m

Chicago Midway

Sat 10/25

11:31 am-3:11 pm

Nonstop2h 40m

$87

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 9/20

6:32 pm-11:17 pm

1 stop5h 45m

Chicago Midway

Sun 9/21

10:13 am-1:55 pm

Nonstop2h 42m

$134

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 9/17

6:31 am-3:58 pm

2 stops10h 27m

Chicago Midway

Sat 9/20

10:51 am-2:33 pm

Nonstop2h 42m

$141

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 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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Orlando, with most prices found around $94. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Orlando during the month February is also very affordable. Most momondo users find prices during this month for around $165.

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. The lowest ticket price found for a Friday departure recently was $180. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $287.

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

Flying to Chicago Midway Airport from Orlando at noon is the least expensive time of day to depart. momondo users have found prices as low as $184 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $289. 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 when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $206 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 for as low as $174 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 to Chicago Midway Airport flight prices changed over time?

As of August 2025, prices for Orlando to Chicago Midway Airport flights are approximately 26% more expensive when compared to flights at the same time last year.

When to book flights from Orlando to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Orlando 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 to Chicago Midway Airport (ORL to MDW) flight deals and tips

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

Best Price Found

$43

Fastest flight time

2h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Orlando in the past 72 hours is $43. The best round-trip flight deal from Orlando to Chicago Midway Airport found on momondo in the last 72 hours is $63.
The fastest flight from Orlando to Chicago Midway Airport takes 2h 45m
Direct flights go from Orlando 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 982.0 mi. Typically, this will take 2h 51m by plane in normal conditions.

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

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

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

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

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

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

Best airlines flying from Orlando to Chicago Midway Airport

Compare and see reviews for airlines that fly from Orlando to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $85Free CancellationRating
5.8
3,212 reviews
Search Frontier flights
DeltaPriceFrom $114Free CancellationRating
8.0
7,986 reviews
Search Delta flights
SouthwestPriceFrom $159Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

  • Southwest Flights From Orlando to Chicago Midway Airport

    Southwest operates around 50 flights from Orlando to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $335, but momondo users have found Southwest deals from Orlando to Chicago Midway Airport from as low as $159 round-trip. Southwest has been scored 8.0/10 in 4,246 reviews.

  • Frontier Flights From Orlando to Chicago Midway Airport

    Another popular option for Orlando to Chicago Midway Airport flights is Frontier (5.8/10, 3,212 ratings). Frontier flies from Orlando to Chicago Midway Airport around 3 times per week, with deals starting from $85 round-trip and rising to an average price of around $170.

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
Lansing
Portage
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?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Orlando.

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

Flights from Orlando to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Orlando to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are not ready to book a flight from Orlando to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago Midway Airport trip

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