MCO - MDW

$53 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 3/10. 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
$87
Overall average: $237
Frontier
Fri 5/15Sun 5/17
MCO - MDW • Non-stop
Cheapest non-stop
$87
Typical prices: $174-$382
Frontier
Fri 5/15Sat 5/16
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
Nonstop flights
Every day
You can fly direct with Frontier and Southwest. Average duration is 2h 55m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Frontier
Most punctual • 82% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 33% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 23% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Fri, May 15 - Sun, May 17
Frontier Logo
6:05 am - 8:04 am
MCO
-
MDW
2h 59mnonstop
Frontier Logo
9:14 am - 1:03 pm
MDW
-
MCO
2h 49mnonstop
$87Frontier
Thu, Apr 30 - Sun, May 3
Frontier Logo
6:05 am - 8:04 am
MCO
-
MDW
2h 59mnonstop
Frontier Logo
9:14 am - 1:03 pm
MDW
-
MCO
2h 49mnonstop
$88Frontier
Thu, Apr 23 - Fri, Apr 24
Frontier Logo
5:30 am - 7:26 am
MCO
-
MDW
2h 56mnonstop
Frontier Logo
6:49 pm - 10:42 pm
MDW
-
MCO
2h 53mnonstop
$91Frontier
Fri, Mar 6 - Mon, Mar 9
Frontier Logo
11:05 am - 1:08 pm
MCO
-
MDW
3h 03mnonstop
Frontier Logo
9:51 pm - 1:38 am
MDW
-
MCO
2h 47mnonstop
$100Frontier
Wed, Mar 11 - Tue, Mar 24
Frontier Logo
4:05 pm - 6:13 pm
MCO
-
MDW
3h 08mnonstop
Frontier Logo
11:19 am - 3:04 pm
MDW
-
MCO
2h 45mnonstop
$101Frontier
Fri, Apr 17 - Mon, Apr 20
Frontier Logo
6:00 am - 7:59 am
MCO
-
MDW
2h 59mnonstop
Frontier Logo
9:14 am - 1:03 pm
MDW
-
MCO
2h 49mnonstop
$104Frontier
Sat, Mar 7 - Tue, Mar 10
Frontier Logo
7:42 pm - 9:45 pm
MCO
-
MDW
3h 03mnonstop
Frontier Logo
11:19 am - 3:04 pm
MDW
-
MCO
2h 45mnonstop
$106Frontier
Tue, Mar 10 - Tue, Mar 17
Frontier Logo
4:05 pm - 6:13 pm
MCO
-
MDW
3h 08mnonstop
Frontier Logo
11:19 am - 3:04 pm
MDW
-
MCO
2h 45mnonstop
$109Frontier
Sat, Mar 7 - Tue, Mar 10
Frontier Logo
11:05 am - 1:08 pm
MCO
-
MDW
3h 03mnonstop
Frontier Logo
11:19 am - 3:04 pm
MDW
-
MCO
2h 45mnonstop
$110Frontier
Sat, Mar 7 - Wed, Mar 11
Frontier Logo
7:42 pm - 9:45 pm
MCO
-
MDW
3h 03mnonstop
Frontier Logo
11:19 am - 3:04 pm
MDW
-
MCO
2h 45mnonstop
$111Frontier
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.

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 $159 (return) on average. On the other hand, the most expensive months are March and April, where the average cost of round-trip tickets is $240 and $240 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, which saves you about 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 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$53
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 17% 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 $53 for a one-way ticket and $87 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, Alaska Airlines, and JetBlue 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.

  • Which airline alliances offer flights from Orlando to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Orlando and Chicago Midway Airport.

  • 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 $286 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 $196 and an overall rating of 7.9.

  • 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 $96 or less one-way and $134 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

Frontier, Southwest

Frontier, Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Frontier, Southwest

Frontier, 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

Frontier, Southwest

Frontier, Southwest

Wednesday

Frontier, Southwest

Frontier, 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

Reviews of the 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 4298 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

An entire day of delays. Cost lots of money. Meals and a hotel.

4.0 OkayLindy, Feb 2026
VPS - DAL
Read more Southwest reviews

An entire day of delays. Cost lots of money. Meals and a hotel.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The flight was great as well as the airline staff

Got on the plane and sat there for an hour before departure.

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

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.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

The experience was good. No frills but I got there safe and sound and on time.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

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

Information on your arrival and departure airports