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Cheap flights from Orlando to Chicago Midway Airport from $50

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 Midway Airport departing on 4/15. 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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Find the cheapest flights from Orlando to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Orlando to Chicago.
10:30 am - 12:31 pmMCO-MDW
3h 01mnonstop
8:00 am - 11:51 amMDW-MCO
2h 51mnonstop
$101Frontier
Find Deal
Fri, Apr 25 - Sun, Apr 27
10:30 am - 12:31 pmMCO-MDW
3h 01mnonstop
1:26 pm - 5:20 pmMDW-MCO
2h 54mnonstop
$104Frontier
Find Deal
Fri, Apr 25 - Mon, Apr 28
10:30 am - 12:31 pmMCO-MDW
3h 01mnonstop
8:00 am - 11:51 amMDW-MCO
2h 51mnonstop
$105Frontier
Find Deal
Fri, Apr 25 - Sun, Apr 27
5:34 pm - 7:35 pmMCO-MDW
3h 01mnonstop
1:23 pm - 5:17 pmMDW-MCO
2h 54mnonstop
$106Frontier
Find Deal
Thu, Apr 17 - Mon, Apr 21
5:34 pm - 7:35 pmMCO-MDW
3h 01mnonstop
1:23 pm - 5:17 pmMDW-MCO
2h 54mnonstop
$107Frontier
Find Deal
Thu, Apr 17 - Mon, Apr 21
6:25 pm - 8:15 pmMCO-MDW
2h 50mnonstop
6:40 pm - 10:15 pmMDW-MCO
2h 35mnonstop
$177Southwest
Find Deal
Wed, May 7 - Sat, May 10
8:00 am - 9:50 amMCO-MDW
2h 50mnonstop
3:20 pm - 10:00 pmMDW-MCO
5h 40m1 stop
$191Southwest
Find Deal
Wed, May 28 - Tue, Jun 3
6:25 pm - 10:22 pmMCO-MDW
4h 57m1 stop
6:04 am - 11:46 amMDW-MCO
4h 42m1 stop
$217Delta
Find Deal
Sat, Apr 26 - Mon, Apr 28
4:45 pm - 9:27 pmMCO-MDW
5h 42m1 stop
12:48 pm - 6:32 pmMDW-MCO
4h 44m1 stop
$229Delta
Find Deal
Sun, May 25 - Wed, May 28
8:32 am - 10:09 amMCO-MDW
26h 37m2 stops
10:48 am - 10:46 pmMDW-MCO
34h 58m2 stops
Thu, May 8 - Sun, May 11

Frontier flights from Orlando to Chicago Midway Airport

Our best Frontier deals on Orlando to Chicago Midway Airport flight tickets
Frontier
Apr 25
MCO10:30 amOrlando
3h 01m
MDW12:31 pmChicago Midway
Apr 27
MDW8:00 amChicago Midway
2h 51m
MCO11:51 amOrlando
Frontier
Apr 25
MCO10:30 amOrlando
3h 01m
MDW12:31 pmChicago Midway
Apr 28
MDW1:26 pmChicago Midway
2h 54m
MCO5:20 pmOrlando
Frontier
Apr 25
MCO10:30 amOrlando
3h 01m
MDW12:31 pmChicago Midway
Apr 27
MDW8:00 amChicago Midway
2h 51m
MCO11:51 amOrlando

Delta flights from Orlando to Chicago Midway Airport

Our best Delta deals on Orlando to Chicago Midway Airport flight tickets
Delta
Apr 26
MCO6:25 pmOrlando
4h 57m
1 stop
MDW10:22 pmChicago Midway
Apr 28
MDW6:04 amChicago Midway
4h 42m
1 stop
MCO11:46 amOrlando
Delta
May 25
MCO4:45 pmOrlando
5h 42m
1 stop
MDW9:27 pmChicago Midway
May 28
MDW12:48 pmChicago Midway
4h 44m
1 stop
MCO6:32 pmOrlando
Delta
Apr 24
MCO2:18 pmOrlando
5h 02m
1 stop
MDW6:20 pmChicago Midway
Apr 26
MDW5:59 pmChicago Midway
4h 17m
1 stop
MCO11:16 pmOrlando

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 February is, on average, the cheapest month to fly to Chicago Midway Airport from Orlando, with most prices found around $87. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Orlando during the month September is also very affordable. Most momondo users find prices during this month for around $164.

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 $159. 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 $273.

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 $173 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $219. 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 23 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $187 when searching 23 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 $81 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 March 2025, prices for Orlando to Chicago Midway Airport flights are approximately 53% more expensive when compared to flights at the same time last year.

Cheap Orlando to Chicago Midway Airport 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

$50

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 $50. The best round-trip flight deal from Orlando to Chicago Midway Airport found on momondo in the last 72 hours is $101.
The fastest flight from Orlando to Chicago Midway Airport takes 2h 45m
Direct flights go from Orlando to Chicago Midway Airport every day.

  • 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 45m 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 $74Free CancellationRating
6.0
3,271 reviews
Search Frontier flights
SouthwestPriceFrom $184Free CancellationRating
8.0
4,274 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
8.0
7,895 reviews
Search Delta flights
  • Southwest Flights From Orlando to Chicago Midway Airport

    Southwest operates around 47 flights from Orlando to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $386, but momondo users have found Southwest deals from Orlando to Chicago Midway Airport from as low as $184 round-trip. Southwest has been scored 8.0/10 in 4,274 reviews.

  • Frontier Flights From Orlando to Chicago Midway Airport

    Another popular option for Orlando to Chicago Midway Airport flights is Frontier (6.0/10, 3,271 ratings). Frontier flies from Orlando to Chicago Midway Airport around 4 times per week, with deals starting from $74 round-trip and rising to an average price of around $148.


Traveling to a place near Chicago?

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


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