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Cheap flights from Orlando (ORL) to Midway (MDW) from $36

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/15. 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.
ORL — MDW
jun. 12 — jun. 191
From?
To?
mié. 6/12
mié. 6/19
1 adult, Economy
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The best prices from Orlando to Chicago Midway are usually found in September or November, booked 41 days in advance, depart on a Thursday or Friday and return on a Thursday

Cheap flight deals from Orlando to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Orlando (ORL) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated junio 7, 2024.

Popular in

July

Cheapest in

September

Round-trip from

$223

One-way from

$106
High demand for flights, 32% potential price rise
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Best time to find cheap flights, 23% potential price drop
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From Orlando (ORL) to Chicago Midway
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One-way flight from Orlando (ORL) to Chicago Midway
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What is the cheapest day to fly round-trip from Orlando to Chicago Midway Airport?

Flights from Orlando to Chicago Midway Airport are found to be more expensive on Saturday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago Midway Airport.

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

Travelers have found it’s best to book a flight 57 days in advance to save up to 243% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 57 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Orlando to Chicago Midway Airport 1-2 weeks in advance for as low as $112, or $248 for flights within the next 24 hours.

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

October is one of the best times of the year to fly to Chicago Midway Airport from Orlando. Prices for October average $152 per person but you can even find prices for as low as $43. The most expensive prices can be found in the month of June. Opting for a October flight can save you 39% on your journey compared to booking in June

What is the cheapest time of day to fly from ORL to MDW?

It’s typically best to fly out from Orlando to Chicago Midway Airport at noon. Doing so could potentially save you 30% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap Orlando to Midway flights in June & July 2024

Find cheap flight options from Orlando to Midway specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,048,502 searches. Prices were last updated on junio 7, 2024.
The lowest fares we've come across on flights traveling from Orlando to Chicago in June and July 2024. Check back soon for alternative fares.
jue. 7/117:35 amMCO - MDW
Nonstop2h 45mFrontier
dom. 7/149:04 pmMDW - MCO
Nonstop2h 40mFrontier
Deal found 6/5$78
jue. 7/117:35 amMCO - MDW
Nonstop2h 45mFrontier
dom. 7/149:04 pmMDW - MCO
Nonstop2h 40mFrontier
Deal found 6/6$81
jue. 7/117:35 amMCO - MDW
Nonstop2h 45mFrontier
vie. 7/126:11 pmMDW - MCO
Nonstop2h 41mFrontier
Deal found 6/6$108
jue. 7/117:35 amMCO - MDW
Nonstop2h 45mFrontier
vie. 7/126:11 pmMDW - MCO
Nonstop2h 41mFrontier
Deal found 6/6$113
jue. 6/277:35 amMCO - MDW
Nonstop2h 56mFrontier
vie. 7/51:11 pmMDW - MCO
Nonstop2h 41mFrontier
Deal found 6/6$118
jue. 7/47:35 amMCO - MDW
Nonstop2h 56mFrontier
jue. 7/119:04 pmMDW - MCO
Nonstop2h 40mFrontier
Deal found 6/6$122
lun. 7/159:20 amMCO - MDW
Nonstop2h 45mFrontier
jue. 8/152:54 pmMDW - MCO
Nonstop2h 41mFrontier
Deal found 6/6$128
vie. 7/510:20 amMCO - MDW
Nonstop2h 45mFrontier
dom. 7/149:04 pmMDW - MCO
Nonstop2h 40mFrontier
Deal found 6/6$129
vie. 7/123:20 pmMCO - MDW
Nonstop2h 45mFrontier
dom. 7/149:04 pmMDW - MCO
Nonstop2h 40mFrontier
Deal found 6/6$135

Orlando to Midway 2024 flight deals

Discover exclusive flight deals for travel between Orlando and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,048,502 searches. Data last updated junio 7, 2024.
The lowest fares we've come across on flights traveling from Orlando to Chicago in June and July 2024. Check back soon for alternative fares.
jue. 8/1512:11 pmMCO - MDW
Nonstop2h 48mFrontier
sáb. 8/2410:08 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 6/6$75
jue. 7/117:35 amMCO - MDW
Nonstop2h 45mFrontier
dom. 7/149:04 pmMDW - MCO
Nonstop2h 40mFrontier
Deal found 6/5$78
vie. 8/23:20 pmMCO - MDW
Nonstop2h 45mFrontier
dom. 8/49:04 pmMDW - MCO
Nonstop2h 40mFrontier
Deal found 6/6$80
jue. 7/117:35 amMCO - MDW
Nonstop2h 45mFrontier
dom. 7/149:04 pmMDW - MCO
Nonstop2h 40mFrontier
Deal found 6/6$81
sáb. 8/317:25 amMCO - MDW
Nonstop2h 48mFrontier
dom. 9/82:54 pmMDW - MCO
Nonstop2h 41mFrontier
Deal found 6/5$82
jue. 8/2212:11 pmMCO - MDW
Nonstop2h 48mFrontier
dom. 8/252:54 pmMDW - MCO
Nonstop2h 41mFrontier
Deal found 6/6$84
jue. 8/2212:11 pmMCO - MDW
Nonstop2h 48mFrontier
dom. 8/252:54 pmMDW - MCO
Nonstop2h 41mFrontier
Deal found 6/6$85
jue. 8/2212:11 pmMCO - MDW
Nonstop2h 48mFrontier
sáb. 8/2410:08 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 6/6$87
jue. 8/1512:11 pmMCO - MDW
Nonstop2h 48mFrontier
sáb. 8/1710:08 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 6/6$88

Orlando to Midway flights leaving soon

Find last-minute flight options from Orlando to Midway for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,048,502 searches. Data last updated junio 7, 2024.
Have a look at some of the last-minute flights available departing from Orlando to Chicago. To prevent any unwanted surprises, users should verify their flight info before booking.
sáb. 6/156:00 amMCO - MDW
Nonstop2h 55mFrontier
sáb. 6/2211:51 amMDW - MCO
Nonstop2h 45mFrontier
Deal found 6/5$160
sáb. 6/156:00 amMCO - MDW
Nonstop2h 55mFrontier
jue. 6/208:51 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 6/4$163
mié. 6/128:00 amMCO - MDW
1 stop7h 34mFrontier
jue. 6/278:51 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 6/5$167
mié. 6/128:00 amMCO - MDW
1 stop7h 34mFrontier
sáb. 6/2211:51 amMDW - MCO
Nonstop2h 45mFrontier
Deal found 6/4$169
jue. 6/137:35 amMCO - MDW
Nonstop2h 56mFrontier
jue. 6/208:51 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 6/4$173
mar. 6/118:00 amMCO - MDW
2 stops14h 20mFrontier
sáb. 6/2211:51 amMDW - MCO
Nonstop2h 45mFrontier
Deal found 6/4$174
mar. 6/114:02 pmMCO - MDW
1 stop8h 04mFrontier
sáb. 6/2211:51 amMDW - MCO
Nonstop2h 45mFrontier
Deal found 6/6$176
jue. 6/207:35 amMCO - MDW
Nonstop2h 56mFrontier
sáb. 6/2211:51 amMDW - MCO
Nonstop2h 45mFrontier
Deal found 6/4$177
mar. 6/116:00 amMCO - MDW
2 stops16h 20mFrontier
jue. 6/208:51 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 6/4$179

One-way flights to Midway from Orlando

Search for one-way flight options from Orlando to Midway. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,048,502 searches. Data last updated junio 7, 2024.
Users traveling one-way from Orlando to Chicago can select one of these great deals. For those needing a return trip from Orlando, there is a search form available above.
jue. 8/1512:11 pmMCO - MDW
Nonstop2h 48mFrontier
Deal found 6/5$36
jue. 7/257:35 amMCO - MDW
Nonstop2h 45mFrontier
Deal found 6/6$39
jue. 7/47:35 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 6/6$41
jue. 7/257:35 amMCO - MDW
Nonstop2h 45mFrontier
Deal found 6/5$42
vie. 9/610:35 amMCO - MDW
Nonstop2h 48mFrontier
Deal found 6/5$48
jue. 6/277:35 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 6/5$49
mar. 8/65:18 pmMCO - MDW
1 stop6h 55mFrontier
Deal found 6/7$52
mar. 8/1312:13 pmMCO - MDW
1 stop9h 57mFrontier
Deal found 6/7$53
lun. 6/249:15 amMCO - MDW
Nonstop2h 55mFrontier
Deal found 6/6$69

Find flights from Orlando to Midway within your budget

Customize your flight search to find flights from Orlando to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 3,048,502 searches. Data last updated junio 7, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$75 - $196

Route

Depart

Return

Price

OrlandoChicago Midway

MCO - MDW

MCOMDW

Orlando

jue. 8/15

Nonstop2h 48m

Chicago Midway

sáb. 8/24

Nonstop2h 41m

$75

OrlandoChicago Midway

MCO - MDW

MCOMDW

Orlando

jue. 7/11

Nonstop2h 45m

Chicago Midway

dom. 7/14

Nonstop2h 40m

$78

OrlandoChicago Midway

MCO - MDW

MCOMDW

Orlando

vie. 8/2

Nonstop2h 45m

Chicago Midway

dom. 8/4

Nonstop2h 40m

$80

OrlandoChicago Midway

MCO - MDW

MCOMDW

Orlando

jue. 7/11

Nonstop2h 45m

Chicago Midway

dom. 7/14

Nonstop2h 40m

$81

OrlandoChicago Midway

MCO - MDW

MCOMDW

Orlando

sáb. 8/31

Nonstop2h 48m

Chicago Midway

dom. 9/8

Nonstop2h 41m

$82

OrlandoChicago Midway

MCO - MDW

MCOMDW

Orlando

jue. 8/22

Nonstop2h 48m

Chicago Midway

dom. 8/25

Nonstop2h 41m

$84

OrlandoChicago Midway

MCO - MDW

MCOMDW

Orlando

jue. 8/22

Nonstop2h 48m

Chicago Midway

dom. 8/25

Nonstop2h 41m

$85

OrlandoChicago Midway

MCO - MDW

MCOMDW

Orlando

jue. 8/22

Nonstop2h 48m

Chicago Midway

sáb. 8/24

Nonstop2h 41m

$87

OrlandoChicago Midway

MCO - MDW

MCOMDW

Orlando

mar. 7/9

1 stop7h 45m

Chicago Midway

sáb. 7/13

1 stop4h 35m

$196

Flights are sorted by cheapest first

Deals found on 6/6

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

Use this chart to determine the optimal time to book a round-trip flight from Orlando to Midway. Price data was last updated on May 31, 2024.
The price you pay for your flight from Orlando to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 41 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Search Deals

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

Use this chart to determine the cheapest time to fly round-trip from Orlando to Midway. Price data was last updated on June 2, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Orlando to Chicago Midway Airport flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Best time to book a flight from Orlando to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Orlando with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Temperature and rainfall in Midway by month

Plan your trip to Midway by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated junio 7, 2024.
Read through reviews of airlines operating flights from Orlando to Chicago, such as Allegiant Air, Frontier and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,363 reviews

Entertainment

8.0

Overall

8.0

Comfort

7.9

Food

7.4

Boarding

8.2

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
10,363 reviews
Delta
8.0
Very good
10,363 reviews

Entertainment

8.0

Overall

8.0

Comfort

7.9

Food

7.4

Boarding

8.2

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

WestJet
7.5
Good
2,853 reviews
Delta
8.0
Very good
10,363 reviews

Entertainment

8.0

Overall

8.0

Comfort

7.9

Food

7.4

Boarding

8.2

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Allegiant Air
7.5
Good
995 reviews
Delta
8.0
Very good
10,363 reviews

Entertainment

8.0

Overall

8.0

Comfort

7.9

Food

7.4

Boarding

8.2

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Porter Airlines
7.4
Good
382 reviews
Delta
8.0
Very good
10,363 reviews

Entertainment

8.0

Overall

8.0

Comfort

7.9

Food

7.4

Boarding

8.2

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Frontier
6.2
Okay
3,977 reviews
Delta
8.0
Very good
10,363 reviews

Entertainment

8.0

Overall

8.0

Comfort

7.9

Food

7.4

Boarding

8.2

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Orlando to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Orlando to Chicago Midway Airport for under $100 on Cheapflights?

    Yes, there are multiple flights from Orlando to Chicago Midway Airport for under $100. The cheapest flight booked recently is on Frontier for just $75, but on average you can expect to pay $97.

  • Are there nonstop flights from Orlando to Chicago Midway Airport for under $100 on Cheapflights?

    Cheapflights has at least 20 direct flights from Orlando to Chicago Midway Airport under $100. A good price for a nonstop flight from Orlando to Chicago Midway Airport is less than $97.

  • Are there last-minute flights available from Orlando to Chicago Midway Airport for under $200?

    There are currently 20+ open flights from Orlando to Chicago Midway Airport within the next 7 days for less than $200.

  • What is the cheapest airline to fly from Orlando to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Orlando to Chicago Midway Airport round-trip from $75. Users have found that Frontier is 51% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Orlando to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $36 on Frontier. Other airlines that offer cheap prices include Allegiant Air from $101 and Delta from $108 one-way.

  • What are the cheapest flights from Orlando to Chicago Midway Airport?

    While on average a flight from Orlando to Chicago Midway Airport is generally $123, our data shows the cheapest flight currently is $38. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $115 for that flight.

  • What does MCO to MDW mean?

    MCO stands for Orlando Airport, while MDW stands for Chicago Midway Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry.

  • Can I find deals for flights from Orlando to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your Orlando to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Orlando to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Orlando to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Orlando to Midway that include hotel bookings?

    Yes. In addition to deals on Orlando to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Orlando to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Orlando to Midway.

  • Can I find deals for business class flights from Orlando to Midway?

    Yes. Cheapflights offers flight deals from Orlando to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Orlando to Midway that allow pets onboard?

    Many airlines flying from Orlando to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Orlando to Midway?

    Yes, you can often find last-minute deals on Orlando to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Orlando to Chicago Midway Airport flight deals updated?

    The Orlando to Chicago Midway Airport flight deals you see on this page were last updated on 6/6.

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

    Currently, December is the cheapest month in which you can book a flight from Orlando to Chicago Midway Airport (average of $141). Flying from Orlando to Chicago Midway Airport in July is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Orlando to Midway
See prices for flight routes from nearby airports that may be better suited for you.

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Top 2 airlines flying from Orlando to Midway

Discover the top 2 airlines that operate flights from Orlando to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 3,048,502 searches. Data last updated junio 7, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$123FlexibilityNo cancel feeOn-time62%
DeltaCheapest$215Average$357FlexibilityNo cancel feeOn-timeN/A
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Chicago to Las Vegas flights
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Search flights from Orlando to Midway by cabin class

Find flights from Orlando to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Orlando to Midway

Find hourly flight availability from Orlando to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated junio 7, 2024.
4%of flight departuresEarly morningMidnight to 6 am
38%of flight departuresMorning6 am to noon
45%of flight departuresAfternoonNoon to 6 pm
13%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Orlando to Midway

Explore weekly flight availability from Orlando to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated junio 7, 2024.
Sunday20daily flights
Monday17daily flights
Tuesday16daily flights
Wednesday16daily flights
Thursday16daily flights
Friday17daily flights
Saturday17daily flights

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