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 11/24. 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
$75
Overall average: $178
Frontier
Fri 1/30Mon 2/2
MCO - MDW • Non-stop
Cheapest non-stop
$74
Typical prices: $189-$383
Frontier
Thu 12/11Mon 12/15
MCO - MDW • Non-stop
Our travelers' advice
AI-generated summary based on content written by travel experts
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
Frontier
Cheapest • from $124 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 40% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 57% price drop
November
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Midway!
Flight Deals
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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, Jan 30 - Mon, Feb 2
Frontier Logo
5:49 pm - 7:52 pmMCO-MDW
3h 03mnonstop
Frontier Logo
1:00 pm - 4:49 pmMDW-MCO
2h 49mnonstop
$75Frontier
Find Deal
Wed, Dec 24 - Thu, Jan 1
Frontier Logo
7:58 pm - 9:58 pmMCO-MDW
3h 00mnonstop
Frontier Logo
3:10 pm - 6:58 pmMDW-MCO
2h 48mnonstop
$77Frontier
Find Deal
Thu, Dec 25 - Wed, Dec 31
Frontier Logo
7:58 pm - 9:58 pmMCO-MDW
3h 00mnonstop
Frontier Logo
3:10 pm - 6:58 pmMDW-MCO
2h 48mnonstop
$82Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
8:40 pm - 10:39 pmMCO-MDW
2h 59mnonstop
Frontier Logo
6:37 pm - 10:23 pmMDW-MCO
2h 46mnonstop
$83Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
7:58 pm - 9:58 pmMCO-MDW
3h 00mnonstop
Frontier Logo
6:37 pm - 10:23 pmMDW-MCO
2h 46mnonstop
$84Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
8:40 pm - 10:39 pmMCO-MDW
2h 59mnonstop
Frontier Logo
6:37 pm - 10:23 pmMDW-MCO
2h 46mnonstop
$87Frontier
Find Deal
Fri, Dec 12 - Mon, Dec 15
Frontier Logo
8:40 pm - 10:39 pmMCO-MDW
2h 59mnonstop
Frontier Logo
6:15 am - 5:27 pmMDW-MCO
10h 12m1 stop
$88Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
7:58 pm - 9:58 pmMCO-MDW
3h 00mnonstop
Frontier Logo
6:37 pm - 10:23 pmMDW-MCO
2h 46mnonstop
$89Frontier
Find Deal
Thu, Dec 25 - Thu, Jan 1
Frontier Logo
7:58 pm - 9:58 pmMCO-MDW
3h 00mnonstop
Frontier Logo
3:10 pm - 6:58 pmMDW-MCO
2h 48mnonstop
$90Frontier
Find Deal
Sat, Dec 6 - Sun, Dec 7
Frontier Logo
8:42 pm - 11:08 amMCO-MDW
15h 26m1 stop
Frontier Logo
6:37 pm - 10:23 pmMDW-MCO
2h 46mnonstop
$91Frontier
Find Deal
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, Friday 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 May, where the average cost of round-trip tickets is $323 and $237 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 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

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.

Southwest

Southwest offers free snacks and soft drinks, plus Wi-Fi for streaming entertainment on most flights.


Southwest's Rapid Rewards program offers unlimited rewards seats and points that never expire.

Airports
MCO

MCO has long security lines; consider booking MCO Reserve for a timeslot in an expedited line. Book early as spots are limited.

MDW

Take the CTA Orange Line from MDW to reach downtown Chicago in about 25-30 minutes, avoiding traffic delays.

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

Good to know

Low seasonFebruary
Cheapest flight$48
Best time to beat the crowds with an average 57% drop in price.
Most popular time to fly and prices are also 11% 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 $48 for a one-way ticket and $74 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, 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 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 $321 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 $216 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 $95 or less one-way and $98 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 4 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 4245 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

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.

2.0 MediocreCharity, Nov 2025MSP - MDW
Read more Southwest reviews

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.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

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.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Non stop on long haul is the way to go. Great experience

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

Cramped seating for me. Luckily it wasn’t a long flight

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Terrible seat, no in flight entertainment. No complimentary food or drinks. Seats really hurt my back after flying spirit for the day.

Had to deplane for undisclosed mechanical issue. Landed in Chicago 3 hours late. Food voucher at FLL came just as we were recording. Crew and agents were troopers--better than Spirit last night.

It was delayed, and the airport had cockroaches jumping on our bags. The flight crew was great, the seats were pretty comfortable.

We spent 5 1/2 hours at Ohare cause our flight was diverted cause of rain in the area. We missed appts that we had set on Tuesday and cause we were flying back the next day on the 7am flight we had no time to reschedule anything. Other airlines were landing and taking off fine having no issues. It was only Spirit. Very frustrating flight and I understand why the flights are only around 25-30% full.

I didn’t mind being delayed due to weather, but continuing to post (and not update) that we would be delayed until after the flight was already supposed to have taken off was a bit much. In the future, please announce the delay even if the time is still unknown.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

Friendly employees, good seat, on time, Great flight. Pilot and attendants greeted passengers as we deplaned. However, I could not ever understand what the flight attendant was saying on the mic. It was too fast, and too loud.

The flight was canceled and was bounced around time wise with my elderly parents. That being said the gentleman in custody service was amazingly helpful

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.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

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

Information on your arrival and departure airports