MCO - MDW

$57 Find Cheap Flights from Orlando to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Orlando to Midway departing on 5/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Orlando to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Orlando to Chicago, as well as popular online travel agencies
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Expert advice
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Flights Deals

Cheap Flight Deals from Orlando to Midway (MCO-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Orlando to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Orlando to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Orlando to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
6:22 pm - 8:17 pmMCO-MDW
2h 55mnonstop
Frontier Logo
9:12 pm - 12:53 amMDW-MCO
2h 41mnonstop
$111Frontier
Find Deal
Thu, Jun 26 - Mon, Jun 30
Frontier Logo
6:20 pm - 8:17 pmMCO-MDW
2h 57mnonstop
Frontier Logo
9:12 pm - 12:53 amMDW-MCO
2h 41mnonstop
$115Frontier
Find Deal
Fri, May 30 - Sun, Jun 1
Frontier Logo
6:20 pm - 8:17 pmMCO-MDW
2h 57mnonstop
Frontier Logo
9:12 pm - 12:53 amMDW-MCO
2h 41mnonstop
$116Frontier
Find Deal
Fri, May 30 - Sun, Jun 1
Frontier Logo
6:23 pm - 8:22 pmMCO-MDW
2h 59mnonstop
Frontier Logo
9:12 pm - 1:03 amMDW-MCO
2h 51mnonstop
$117Frontier
Find Deal
Thu, Jul 17 - Mon, Jul 21
Southwest Logo
2:40 pm - 7:30 pmMCO-MDW
5h 50m1 stop
Southwest Logo
3:40 pm - 10:05 pmMDW-MCO
5h 25m1 stop
$212Southwest
Find Deal
Wed, Jun 4 - Sat, Jun 7
Southwest Logo
6:25 pm - 8:15 pmMCO-MDW
2h 50mnonstop
Southwest Logo
7:05 pm - 10:45 pmMDW-MCO
2h 40mnonstop
$215Southwest
Find Deal
Wed, Jun 4 - Sat, Jun 7
Delta Logo
6:15 am - 12:29 pmMCO-MDW
7h 14m1 stop
Delta Logo
9:25 am - 4:46 pmMDW-MCO
6h 21m1 stop
$217Delta
Find Deal
Sat, Jul 19 - Wed, Jul 23
Southwest Logo
8:50 pm - 10:40 pmMCO-MDW
2h 50mnonstop
Southwest Logo
3:20 pm - 7:00 pmMDW-MCO
2h 40mnonstop
$223Southwest
Find Deal
Thu, May 22 - Sun, May 25
Delta Logo
8:50 am - 12:29 pmMCO-MDW
4h 39m1 stop
Delta Logo
6:00 am - 12:02 pmMDW-MCO
5h 02m1 stop
$235Delta
Find Deal
Tue, Aug 5 - Mon, Aug 11
Delta Logo
4:50 pm - 9:45 pmMCO-MDW
5h 55m1 stop
Delta Logo
6:47 pm - 1:19 amMDW-MCO
5h 32m1 stop
$237Delta
Find Deal
Tue, Jun 17 - Fri, Jun 20
Expert advice

Expert advice for your flight from Orlando to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Frontier

Frontier's Economy Bundle includes a carry-on bag and Standard seat choice, saving on extra fees.


Avoid airport check-in fees by using Frontier's app or kiosk for free check-in.

Read more about Frontierby Stefanie Waldek
Southwest

Southwest offers two free checked bags up to 50 pounds each, ideal for family travel.


Download the Southwest app for free in-flight messaging and entertainment streaming.

Read more about Southwestby Blane Bachelor
Airports
MCO

MCO has long security lines. Consider booking MCO Reserve for a timeslot in an expedited line, available up to seven days before your flight.

Read more about MCOby Stefanie Waldek
MDW

Take the CTA Orange Line from MDW to downtown Chicago. It's a quick 25-30 minute ride, avoiding traffic issues.

Read more about MDWby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier, MDW and MCO

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Useful Info

KAYAK's insights & trends for Orlando to Midway flights

Get data-powered insights and trends into flights from Orlando to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Orlando to Chicago Midway Airport?

The average price of all round-trip flights from Orlando Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Orlando to Chicago Midway Airport, look for departures on Fridays and avoid leaving on a Tuesday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Saturday is the cheapest day to fly and Wednesday is the most expensive.

What is the cheapest month to fly from Orlando Airport to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Orlando Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Orlando Airport to Chicago Midway Airport is February, where tickets cost $87 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $323 and $227 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Orlando Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Orlando Airport to Chicago Midway Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonFebruary
High seasonApril
Cheapest flight$57
Best time to beat the crowds with an average 56% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Orlando to Chicago Midway Airport

When to book flights from Orlando to Midway

Are your dates flexible? Find out the best times to travel from Orlando to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Orlando to Chicago Midway Airport flights

  • Which airline has the most favorable carry-on policy on the Orlando to Chicago route?

    Airlines from Orlando to Chicago Midway Airport have varying or similar luggage requirements. However, all airlines require your bags to fit beneath your seat or in the upper cabin for a smooth journey. If you need an airline with the most favorable carry-on option on this route, consider booking Delta Air Lines.

  • What are the popular layovers on flights from Orlando to Chicago?

    Some airlines fly nonstop from Orlando to Chicago Midway Airport. However, some airlines, including Frontier and Volaris, have a layover. Therefore, check the flight route before booking to know what to expect about the layover city and duration. This also helps you to avoid extended layovers for your journey. Most airlines on this route have a layover in Atlanta.

  • Which airlines offer an eco-friendly journey from Orlando to Chicago Midway Airport?

    Southwest Airlines is environmentally conscious and plans to replace 10% of its total fuel with sustainable aviation fuel by 2030. The company aims to achieve net-zero carbon emissions by 2050 through route optimization and fleet modernization. Volaris has also implemented sustainable practices to lower its carbon footprint. The decarbonization strategies include using sustainable aviation fuels and closely monitoring fuel consumption to ensure fuel efficiency.

  • How can I travel from Chicago Midway Airport to Downtown Chicago?

    You can take the Orange Line train via the subway to reach the city in about 28 minutes. Another option is the Line 60 bus line, which gets you downtown in approximately 1h 25 min, depending on stops and city traffic. If traveling at night, the Line 62 bus offers a reliable journey, arriving in the city in around 43 minutes. Finally, you can take a taxi or rent a car if you need a private trip on this journey.

  • What is the cheapest flight from Orlando Airport to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Orlando Airport to Chicago Midway Airport was $57 for a one-way ticket and $111 for a round-trip.

  • Do I need a passport to fly between Orlando and Chicago Midway Airport?

    A passport is not required to fly from Orlando to Chicago Midway Airport.

  • Which airlines offer Wi-Fi service onboard planes from Orlando to Chicago Midway Airport?

    American Airlines, Delta, JetBlue, and Alaska Airlines offer inflight Wi-Fi service on the Orlando to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Orlando to Chicago Midway Airport?

    The Airbus A320neo is the aircraft model that flies most regularly on the Orlando to Chicago Midway Airport flight route.

  • On which days can I fly direct from Orlando to Chicago Midway Airport?

    There are nonstop flights from Orlando to Chicago Midway Airport on a daily basis.

  • Which is the best airline for flights from Orlando to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Orlando to Chicago are Southwest and Delta. With an average price for the route of $375 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $307 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Orlando to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Orlando to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Orlando to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Orlando is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Orlando to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Orlando with another airline. Booking your flights between Orlando and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Orlando to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Orlando up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Orlando Airport to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $115 or less one-way and $177 or less round-trip.
  • Orlando International Airport (MCO) is a hub for Silver Airways. Chicago Midway International Airport (MDW) is a hub for Southwest Airlines. Both of these airports link many cities, serving millions of passengers annually.
  • The best way to travel from Orlando city center to MCO airport is by boarding the Line 11 bus. The bus gets you there in about 37 minutes. If you need a quick journey, consider a rental car or a taxi to arrive there in around 19 minutes.
  • Passengers who need a special meal on cheap flights from Orlando to Chicago Midway Airport can book Delta Air Lines. These airlines offer a wide range of special dishes, including vegetarian and diabetic meals, to meet the dietary needs of their passengers. However, you must order up to 24 hours before departure.
  • MCO airport offers VIP services to military personnel and other notable travelers. These services include access to the VIP lounge, priority check-in and boarding, meet and greet upon arrival, chauffeur services, and luggage assistance.
  • If traveling on a tight budget from Orlando to Chicago, you can compare prices for cheap flights on this route. Most airlines, including Volaris, Delta, and Frontier, offer low-cost and competitive prices.

Prefer to fly direct from Orlando to Chicago Midway Airport?

Find which airlines fly direct from Orlando Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Orlando to Chicago Midway

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights

Direct returns

Chicago Midway to Orlando

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights
See more direct flights

Top 3 airlines serving from Orlando to Midway

 
See real verified KAYAK customer reviews for airlines flying from Orlando to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Orlando to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4294 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

6.0 GoodJennifer, Apr 2025FLL - RDU
Read more Southwest reviews

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

I like that it was on time and the staff was friendly.

Glad flight made it out. So many delays due to hurricane. everyone did a great job.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Everything was great. Great service, excellent communication, and early arrival

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

Great - This was the last flight before hurricane closures and did a quick turnaround to get the plane heading north. Much appreciated.

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

They switched my flight to Spirit, Never using Kayak again,

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

Asked for a seat change to be w my wife at the gate they were great in sorting it out to make it happen

They cancelled the flight and did nothing. I should be compensated for my uber rides to and from airport. Not a good service by frontier or kayak.

The worst service , the agents from the counter are really bad . Poor customer service . They didnt help me to get in the flight . I was on line when they close the flight without telling and I couldn’t board the plane . I will like to get my money back ey back because it was their fault. Really bad management , bad manners, bad additud

The check in process was a mess for no reason. I spent an hour waiting in line trying to get them to print my boarding pass and as a result I missed my flight.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

Everything you need to know for your flight from Orlando to Midway

Information on your arrival and departure airports

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