$111 Find Cheap Flights from Orlando to Chicago Midway Airport - Compare and Save

These are the earliest and latest flight times available from Orlando Airport to Chicago Midway Airport:

• Earliest: departs at 6:20 am and lands at 9:16 am
• Latest: departs at 10:50 pm and lands at 1:46 am.

The flight takes about 2h 56m.

Two cabin classes are available on flights from Orlando Airport to Chicago Midway Airport:

• Economy Class
• Premium Economy Class

A nonstop flight from Orlando Airport to Chicago Midway Airport takes 2h 56m, covering 990 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

Round-trip flights from Orlando Airport to Chicago Midway Airport range from $148 to $359, with an average of $246 over the past 12 months. Anything below $148 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 12% above the $246 route average. Book 5 weeks before departure for the lowest fares.

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $250 round-trip, compared to $291 via a layover through Atlanta Hartsfield-Jackson (ATL).

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Airbus A321neo family is used most often on this route, operated mainly by Frontier and United Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

Morning is the busiest departure period on Orlando Airport to Chicago Midway Airport flights, with 29% of flights leaving in that window. Afternoon departures account for 29%, evening flights for 28%, and night flights for 14%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $203 to $1,438. That means the highest observed fare was about 7x higher than the lowest one.

JetBlue is the only airline on the Orlando Airport to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

One-way fares from Orlando Airport to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $135, which is 26% below the typical average for this route.

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Flights from Orlando Airport to Chicago Midway Airport usually depart from Orlando (MCO) and arrive at Chicago Midway (MDW).

Morning flights have the fewest delays on this route, while evening departures tend to have the most.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Orlando Airport to Chicago Midway Airport route, 24% of flights were delayed in the past 3 months, with delays averaging 2h 23m.

One-stop flights from Orlando Airport to Chicago Midway Airport most commonly connect through:

• Atlanta Hartsfield-Jackson (ATL) - 95% of one-stop connections
• Dallas/Fort Worth (DFW) - 2% of one-stop connections
• Detroit Metropolitan Wayne County (DTW) - 2% of one-stop connections

Yes. Flexible dates can save you up to 35% on flights from Orlando Airport to Chicago Midway Airport. Friday is the cheapest departure day at $194 round-trip on average, while Wednesday is the most expensive at $297, a difference of $103.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

2 airlines operate flights between Orlando Airport and Chicago Midway Airport. The airlines offering nonstop flights on this route include:

• Southwest
• Frontier

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 44m, compared with 7h 05m via Atlanta Hartsfield-Jackson (ATL) and 8h 48m via Dallas/Fort Worth (DFW).

Chicago Midway Airport is 1 hour behind Orlando Airport (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

Among airlines operating Orlando Airport to Chicago Midway Airport flights:

• Southwest: offers free seat selection
• Frontier: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag and a checked bag in Economy Class
• Frontier: a cabin bag in Economy Class class
• JetBlue: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

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.

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.

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.

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.