Cheap flights from Orlando to Midway (ORL - MDW)

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How to find the cheapest flight from
Orlando (ORL) to Midway (MDW)

All the information you need to plan the best ORL to MDW flight in 2022: compare Orlando to Midway flight prices with the expected peak season, weather and rainfall in Midway.
MCO - MDW
Price
$127 - $358
MDW
Temperature
23 - 73.4 °F
MDW
Rainfall
1.7 - 4.9 inches

Popular in

June

High demand for flights, 30% potential price rise

Cheapest in

February

Best time to find cheap flights, 49% potential price drop

Round-trip from

$127

From Orlando to Chicago Midway

One-way from

$108

One-way flight from Orlando to Chicago Midway

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest month to fly from Orlando to Chicago Midway Airport?

Our data shows that October tends to be the cheapest month to fly to Chicago Midway Airport from Orlando. Users have commonly found prices around $188 for the month, but tickets can be as low as $58. Due to multiple factors, prepare for potentially higher prices in June.

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 51 days in advance to save up to 36% 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 51 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 $216, or $243 for flights within the next 24 hours.

When is the cheapest time to fly from Orlando to Chicago Midway Airport (MCO - MDW)?

When flying from Orlando to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Orlando to Midway in August, September 2022

The best prices found for ORL to MDW flights for August, September
3 Sep - 7 Sep
$127pp
MCO
Orlando
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
MCO
Orlando
7 Sep - 21 Sep
$130pp
MCO
Orlando
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
MCO
Orlando
23 Sep - 27 Sep
$134pp
MCO
Orlando
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
MCO
Orlando

Orlando to Midway 2022 flight deals

Cheap flights to Midway from Orlando found for this year
3 Sep - 7 Sep
$127pp
MCO
Orlando
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
MCO
Orlando
7 Sep - 21 Sep
$130pp
MCO
Orlando
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
MCO
Orlando
23 Sep - 27 Sep
$134pp
MCO
Orlando
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
MCO
Orlando

Cheap Delta flights from Orlando to Midway

16 Aug - 23 Aug
$237pp
MCO
Orlando
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
MCO
Orlando
16 Aug - 18 Aug
$358pp
MCO
Orlando
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
MCO
Orlando
13 Aug - 16 Aug
$371pp
MCO
Orlando
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
MCO
Orlando

Cheap Frontier flights from Orlando to Midway

3 Sep - 7 Sep
$127pp
MCO
Orlando
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
MCO
Orlando
7 Sep - 21 Sep
$130pp
MCO
Orlando
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
MCO
Orlando
23 Sep - 27 Sep
$134pp
MCO
Orlando
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
MCO
Orlando

Non-stop flights to Midway from Orlando

Save time with Orlando to Midway direct flight deals
23 Sep - 27 Sep
$134pp
MCO
Orlando
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
MCO
Orlando
23 Sep - 25 Sep
$139pp
MCO
Orlando
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
MCO
Orlando
24 Sep - 30 Sep
$140pp
MCO
Orlando
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
MCO
Orlando

Last minute flights from Orlando to Midway

Late deals on round-trip flights to Midway from Orlando, departing today and this week
16 Aug - 23 Aug
$178pp
MCO
Orlando
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
MCO
Orlando
16 Aug - 23 Aug
$179pp
MCO
Orlando
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
MCO
Orlando
16 Aug - 23 Aug
$181pp
MCO
Orlando
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
MCO
Orlando

One-way flights to Midway from Orlando

The cheapest one-way flights from Orlando to Midway
12:43 pm - 6:48 pm
Delta
1 Stop
7h 05m
MCO - MDW
Delta
$108
Delta
3:55 am - 9:05 am
Multiple Airlines
2 Stops
30h 10m
MCO - MDW
Multiple Airlines
$111
Kiwi.com
9:23 am - 1:17 am
Frontier
2 Stops
16h 54m
MCO - MDW
Frontier
$114
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Orlando</span> to <span class="emphasized">Midway</span> flights.

Flight FAQs

From Orlando to Midway

Which airlines flying from Orlando to Chicago Midway have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like Delta, Spirit Airlines, and United Airlines flying from Orlando to Chicago Midway have implemented new flexible cancellation policies.

Can I find flights from Orlando to Chicago Midway Airport for under $200 on Cheapflights?

Yes, there are multiple flights from Orlando to Chicago Midway Airport for under $200. The cheapest flight booked recently is on Frontier for just $127, but on average you can expect to pay $144.

Are there nonstop flights from Orlando to Chicago Midway Airport for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Orlando to Chicago Midway Airport under $200. A good price for a nonstop flight from Orlando to Chicago Midway Airport is less than $196.

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 $127. Users have found that Frontier is 49% cheaper than the other options available to this destination.

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

While on average a flight from Orlando to Chicago Midway Airport is generally $281, our data shows the cheapest flight currently is $18. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $127 for that flight.

What are the most popular airlines that fly from Orlando to Chicago Midway Airport?

Before booking your flight from Orlando to Chicago Midway Airport check out the most popular airlines for this route: American Airlines, Alaska Airlines or Delta.

COVID Restrictions

View COVID Travel Restrictions for Midway (MDW)

Do I need a COVID test to fly to Midway from Orlando?

Information is based on travel restrictions for travel to Chicago Midway within the United States

Most visitors from Orlando need to provide a negative COVID-19 test result and/or quarantine to enter Chicago Midway.

COVID-19 testing requirements
Visitors from Orlando are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago Midway.

Quarantine requirements
Visitors from Orlando are not required to quarantine after entering Chicago Midway.

Do I need a test to fly back to Orlando from Midway?

Returning to Orlando from Chicago Midway

COVID-19 testing requirements
Visitors from Chicago Midway are not required to present a negative COVID-19 PCR test or antigen result upon entering Orlando.

Quarantine requirements
Visitors from Chicago Midway are not required to quarantine after entering Orlando.

Hide COVID Travel Restrictions for Midway (MDW)

Alternative routes for Orlando to Midway

See prices for flight routes from nearby airports that may be better suited for you.

Top 5 airlines flying from Orlando to Chicago Midway

The chart below displays the airlines Cheapflights users traveling from Orlando to Midway choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Spirit Airlines
$75 $154 No cancel fee 65%
United Airlines
$132 $230 No cancel fee 69%
Frontier
$142 $264 No cancel fee 62%
Delta
$180 $462 No cancel fee N/A
American Airlines
$187 $393 No cancel fee 71%

Hourly flight availability from Orlando to Midway

See what time of day planes typically take off from Orlando towards Midway.
Morning 6 AM to noon 45% of ORL to MDW departures
Afternoon Noon to 6 PM 30% of ORL to MDW departures
Evening 6 PM to midnight 15% of ORL to MDW departures
Early morning Midnight to 6 AM 10% of ORL to MDW departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Orlando to Midway
See how many times per day planes take to the skies headed from Orlando to Midway.
Sunday
10 daily flights
Monday
10 daily flights
Tuesday
10 daily flights
Wednesday
10 daily flights
Thursday
10 daily flights
Friday
10 daily flights
Saturday
18 daily flights