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MCO - MDW

$35 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 8/8. 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
0 bags
Mon 6/3
Mon 6/10

Search 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
In the last 7 days travelers have searched 43,693,958 times on KAYAK, and here is why:

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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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
5:01 am - 6:54 amMCO-MDW
2h 53mnonstop
7:49 am - 11:37 amMDW-MCO
2h 48mnonstop
$55Frontier
Find Deal
Wed, May 22 - Wed, May 29
12:11 pm - 1:59 pmMCO-MDW
2h 48mnonstop
10:08 am - 1:49 pmMDW-MCO
2h 41mnonstop
$63Frontier
Find Deal
Thu, Aug 15 - Sat, Aug 24
6:15 pm - 8:13 pmMCO-MDW
2h 58mnonstop
7:49 am - 11:37 amMDW-MCO
2h 48mnonstop
$67Frontier
Find Deal
Sat, May 18 - Wed, May 29
5:01 am - 6:54 amMCO-MDW
2h 53mnonstop
7:49 am - 11:37 amMDW-MCO
2h 48mnonstop
$68Frontier
Find Deal
Wed, May 22 - Sun, May 26
5:01 am - 6:54 amMCO-MDW
2h 53mnonstop
8:56 pm - 12:47 amMDW-MCO
2h 51mnonstop
$71Frontier
Find Deal
Wed, May 22 - Mon, Jun 3
5:01 am - 6:54 amMCO-MDW
2h 53mnonstop
8:56 pm - 12:47 amMDW-MCO
2h 51mnonstop
$77Frontier
Find Deal
Wed, May 29 - Mon, Jun 3
5:01 am - 6:54 amMCO-MDW
2h 53mnonstop
8:53 pm - 12:41 amMDW-MCO
2h 48mnonstop
$80Frontier
Find Deal
Wed, May 29 - Sun, Jun 9
5:01 am - 6:54 amMCO-MDW
2h 53mnonstop
1:15 pm - 5:03 pmMDW-MCO
2h 48mnonstop
$85Frontier
Find Deal
Wed, May 22 - Fri, May 31
5:30 am - 10:11 amMCO-MDW
5h 41m1 stop
9:32 am - 3:34 pmMDW-MCO
5h 02m1 stop
$202Delta
Find Deal
Sun, May 26 - Tue, May 28
6:15 am - 9:51 amMCO-MDW
4h 36m1 stop
5:45 pm - 11:18 pmMDW-MCO
4h 33m1 stop
$208Delta
Find Deal
Sat, Jun 29 - Sat, Jul 6

Flights from Orlando to Midway - Travel Insights & Trends

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 flights from Orlando Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
When flying from Orlando to Chicago Midway Airport, you should consider leaving on a Thursday and avoid Sundays if you are looking for the best rates. For your return to Orlando, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

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 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 April, where tickets cost $116 on average. On the other hand, the most expensive months are July and June, where the average cost of tickets is $233 and $190 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Orlando Airport to Chicago Midway Airport, you should book around 5 days before departure. For the absolute cheapest price, our data suggests you should book 70 days before departure.

Which airlines provide the cheapest flights from Orlando to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($35) and Delta ($98). The cheapest round-trip tickets were found on Frontier ($55) and Delta ($202).

Which airlines fly non-stop between Orlando Airport and Chicago Midway Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Orlando Airport to Chicago Midway Airport.
There are 2 airlines that fly nonstop from Orlando Airport to Chicago Midway Airport. They are Frontier and Southwest. The cheapest airline for this route is Frontier, with the best one-way deal found costing $68. On average, the best prices for this route can be found at Frontier.

How many flights are there between Orlando Airport and Chicago Midway Airport per day?

Each day, there are between 8 and 15 nonstop flights that take off from Orlando Airport and land in Chicago Midway Airport, with an average flight time of 2h 47m. The most common departure time is 8:00 pm and most flights take off in the morning. Each week, there are 71 flights. The most frequent day of departure is Tuesday, when 21% of all weekly flights depart. The fewest flights depart on a Friday.

Which cabin class options are there for flights between Orlando Airport and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Orlando to Chicago Midway Airport take?

Direct flights cover the 990 miles separating Orlando to Chicago Midway Airport in about 2h 45m.

What’s the earliest departure time from Orlando to Chicago Midway Airport?

Early birds can take the earliest flight from Orlando Airport at 5:01 am and will be landing in Chicago Midway Airport at 6:54 am.

What’s the latest departure time from Orlando to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Orlando Airport to Chicago Midway Airport jets off at 10:35 pm and lands at 12:20 am.

Good to know

Low season

February

High season

November

Cheapest flight

$35
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 7% 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 $35 for a one-way ticket and $55 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, 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 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, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Orlando to Chicago are Delta and Frontier. With an average price for the route of $378 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $150 and an overall rating of 6.2.

  • 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.

See more FAQs

Top tips for finding a cheap flight from MCO to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $79 or less one-way and $101 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.
See more tips

Prefer to fly non-stop from Orlando to Chicago Midway Airport?

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

Nonstop departures

Orlando to Chicago Midway

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Southwest

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

Nonstop returns

Chicago Midway to Orlando

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Southwest

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
See more direct flights

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
DeltaOverall score based on 10848 reviews
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

6.0 GoodJames, Apr 2024TPA - RDU
Read more about Delta reviews

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

Aircraft very cramped. Check-in was great with an agent helping us. Food was almost non-existent. Pre-flight went well once I got the app reloaded on my phone since we don’t fly much anymore.

I like that it got us where we were going. Everything else needed work. It was 1/2 hour late and we took off an hour late. The plane had to be cleaned and the disabled loaded on board before we could take off which took forever and then we sat at the terminal FOREVER before we took off. The ride was so bumpy that they couldn’t serve drinks and snack but to about 1/2 the plane. Seriously we should have flown out of Fort Lauderdale. We probably would’ve gotten home several hours earlier.

Flight was on time, the staff was personable & professional, & the plane arrived on time.

Flight was great. DELTA did a fantastic job! FLL airport was chaotic!

Crew members are very rude and not cooperate with passengers.

They lost my baggage on my connection flight, it’s been 24 hours since I put my claim in and still no update on my bags.

The flight was canceled, then delayed twice, we were moved gates twice. Short staff at the counter and check in. We waited for our flight 9 hours. Will never use Frontier ever again, or Spirit.

Good - Leg spar, cleanliness, and on time performance. Bad - No snacks and entertainment.

The plane was on time. Boarding went fast. Smooth flight and landing. I filled out info for a frontier credit card on the flight from Indy to Orlando and have have heard nothing back. I was supposed to get all these “instant” rewards and have received nothing g.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

The only thing that may be concerning to others is the multiple notifications of a delayed flight. Then, with less than an hour before boarding, the flight was on time. The gate changed several times, leading to confusion.

The flights were right on time. The issue that was the most difficult was the lack of legroom on the planes

Nothing I missed my first flight because my boarding pass said one thing and another passenger on the same flight said another. I didn’t get notified of a gate change until 8:39 pm which was one minute before the flight departed at 8:40pm when we explained this to gate agent Dorsey prior to the flight departing she was extremely short and had nasty attitude. Some of the passengers in my party including myself needed to catch that flight due work the next which included presentations and court litigation. We were deeply saddened and frustrated how Frontier handled this situation. We were told that the flight was over booked by 19 seats and they constantly change gates to make people miss their flight. If that is true I will ensure there will be a class action lawsuit against frontier airlines.

There was only room for a quarter of the passengers to sit at the gate at MCO. The gate attendant allowed people who did not require assistance to board early before they realized and started to turn people back. The flight was extremely uncomfortable due to pressure. My ears, eyes, sinuses and joints were very painful the whole flight. My sister also complained about her ears and sinuses as well as joints and while deplaning I heard several other passengers complain about the same issues. I’ve never felt that much discomfort flying before and I’ve been doing it for over 40 years.

Book cheap flights from Orlando to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Orlando to Chicago found on KAYAK in the last 72 hours.
8/8Thu
nonstopFrontier
2h 48mMCO-MDW
$35
8/9Fri
nonstopFrontier
2h 48mMCO-MDW
$36
6/4Tue
1 stopDelta
5h 31mMCO-MDW
$98
5/23Thu
1 stopDelta
7h 10mMCO-MDW
$124
7/12Fri
1 stopAllegiant Air
7h 02mMCO-MDW
$135
8/2Fri
1 stopAllegiant Air
6h 25mMCO-MDW
$151
5/16Thu
2 stops
22h 44mMCO-MDW
$154
7/4Thu
2 stops
12h 00mMCO-MDW
$177
7/2Tue
2 stopsPorter Airlines
20h 42mMCO-MDW
$365
8/1Thu
2 stopsPorter Airlines
20h 42mMCO-MDW
$414

Search by stops

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Last minute flights from Orlando to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Orlando to Chicago that are departing in the next 10 days.
5/4Sat
nonstopFrontier
2h 57mMCO-MDW
5/11Sat
nonstopFrontier
3h 00mMDW-MCO
$137
5/4Sat
nonstopFrontier
2h 57mMCO-MDW
5/13Mon
multi-stopFrontier
29h 56mMDW-MCO
$181
5/4Sat
nonstopFrontier
2h 57mMCO-MDW
5/13Mon
nonstopFrontier
2h 56mMDW-MCO
$183
5/4Sat
multi-stopDelta
6h 20mMCO-MDW
5/7Tue
multi-stopDelta
5h 23mMDW-MCO
$316
5/4Sat
multi-stopDelta
4h 44mMCO-MDW
5/12Sun
multi-stopDelta
4h 50mMDW-MCO
$332
5/6Mon
multi-stop
10h 41mMCO-MDW
5/13Mon
multi-stop
22h 42mMDW-MCO
$672
5/6Mon
multi-stop
10h 41mMCO-MDW
5/13Mon
multi-stop
16h 05mMDW-MCO
$734
5/4Sat
multi-stopPorter Airlines
15h 32mMCO-MDW
5/8Wed
multi-stopPorter Airlines
10h 44mMDW-MCO
$1,341
5/4Sat
multi-stopWestJet
15h 36mMCO-MDW
5/8Wed
multi-stopWestJet
18h 50mMDW-MCO
$1,476
5/4Sat
multi-stopWestJet
15h 36mMCO-MDW
5/7Tue
multi-stopWestJet
19h 15mMDW-MCO
$1,717

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Orlando - Chicago Midway Airport Flights

Departure:

Orlando (MCO)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Orlando

Cabin classes:

$77