MCO - MDW

$86 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 6/24. 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
1 adult, Economy, 0 bags

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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Everything you should know

Cheapest round-trip
$171
Typical prices: $310-$173
Southwest
Tue 7/21Wed 7/29
MCO - MDW • Non-stop
Cheapest one-way
$86
Typical prices: $113-$209
Southwest
Wed 6/24
MCO - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Frontier's Economy Bundle includes a carry-on bag.
Expect long security lines at Orlando Airport.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $171 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 49m
Direct flights
Direct flights
+1
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Direct flights
Direct flights
+1
Avoid delays
Most punctual • 77% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $360 (round-trip)
Shortest trip • 5h 28m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 23% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 28% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Orlando to Midway

Tue, Jul 21 - Wed, Jul 29
Southwest Logo
2:30 pm - 4:20 pm
MCO
-
MDW
2h 50mnonstop
Southwest Logo
5:30 pm - 9:20 pm
MDW
-
MCO
2h 50mnonstop
$171Southwest
Tue, Jul 21 - Wed, Jul 29
Southwest Logo
4:40 pm - 7:50 pm
MCO
-
MDW
4h 10m
1 stop
Southwest Logo
8:10 pm - 11:50 pm
MDW
-
MCO
2h 40mnonstop
$177Southwest
Wed, Jul 1 - Tue, Jul 14
Southwest Logo
6:20 am - 11:00 am
MCO
-
MDW
5h 40m
1 stop
Southwest Logo
4:40 pm - 8:25 pm
MDW
-
MCO
2h 45mnonstop
$181Southwest
Tue, Jul 21 - Wed, Jul 29
Southwest Logo
4:40 pm - 7:50 pm
MCO
-
MDW
4h 10m
1 stop
Southwest Logo
3:00 pm - 7:55 pm
MDW
-
MCO
3h 55m
1 stop
$182Southwest
Wed, Jul 1 - Tue, Jul 14
Southwest Logo
10:20 am - 2:10 pm
MCO
-
MDW
4h 50m
1 stop
Southwest Logo
3:00 pm - 7:55 pm
MDW
-
MCO
3h 55m
1 stop
$186Southwest
Wed, Aug 12 - Sat, Aug 15
Southwest Logo
5:25 pm - 7:15 pm
MCO
-
MDW
2h 50mnonstop
Southwest Logo
3:40 pm - 7:15 pm
MDW
-
MCO
2h 35mnonstop
$187Southwest
Tue, Jul 21 - Wed, Jul 22
Southwest Logo
7:10 am - 9:00 am
MCO
-
MDW
2h 50mnonstop
Southwest Logo
8:10 pm - 11:50 pm
MDW
-
MCO
2h 40mnonstop
$189Southwest
Wed, Jul 1 - Tue, Jul 7
Southwest Logo
6:20 am - 11:00 am
MCO
-
MDW
5h 40m
1 stop
Southwest Logo
12:50 pm - 6:45 pm
MDW
-
MCO
4h 55m
1 stop
$191Southwest
Wed, Aug 12 - Sat, Aug 15
Southwest Logo
5:25 pm - 7:15 pm
MCO
-
MDW
2h 50mnonstop
Southwest Logo
7:50 am - 12:55 pm
MDW
-
MCO
4h 05m
1 stop
$193Southwest
Tue, Jul 21 - Wed, Jul 29
Southwest Logo
4:40 pm - 7:50 pm
MCO
-
MDW
4h 10m
1 stop
Southwest Logo
4:40 pm - 8:25 pm
MDW
-
MCO
2h 45mnonstop
$195Southwest
Booking Insights

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.

How much is a round-trip flight from Orlando Airport to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Orlando Airport to Chicago Midway Airport departing in July.

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, Thursday 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 November, where tickets cost $160 (return) on average. On the other hand, the most expensive months are April and May, where the average cost of round-trip tickets is $397 and $292 respectively.

Can I save money by flying with a layover from Orlando Airport to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $304, prices are generally cheapest when you fly direct.

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, which saves you about 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Expert advice

Expert advice for your flight from Orlando to Midway

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier, MDW and MCO

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.

Blane Bachelor

Blane Bachelor

Expert on Southwest

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.

Good to know

Low seasonJanuary
Cheapest flight$86
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 24% lower on average.
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 $86 for a one-way ticket and $171 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, JetBlue, Alaska Airlines, and Delta 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 Boeing 737 MAX 8 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 Frontier?

    The two airlines most popular with KAYAK users for flights from Orlando to Chicago are Southwest and Frontier. With an average price for the route of $300 and an overall rating of 7.9, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $164 and an overall rating of 5.6.

  • 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 $192 or less one-way and $297 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?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Orlando to Chicago Midway.
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

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Orlando

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airlines flying 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 4266 reviews
7.0Food
7.5Entertainment
8.0Comfort
8.1Boarding
8.6Crew
Airline reviews

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

8.0 ExcellentAnonymous, May 2026
BDL - MDW
Read more Southwest reviews

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

It was an early flight and most people napped/slept and the crew let us which was nice.

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

Flight got delayed for 5 hours no good explanation was offered ;(

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

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

Information on your arrival and departure airports