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175 € Cheap Flights from Orlando to Chicago Midway

Compare Orlando to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from Orlando to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Orlando to Chicago Midway Airport? If you want to travel next month, return fares start from 180 €. Find the lowest prices on one-way and return tickets right here.
Chicago.175 € per passenger.Departing Sat, 5 Sep, returning Sat, 12 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Sat, 5 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 12 Sep, arriving in Orlando International.Price includes taxes and charges.From 175 €, select.
Chicago.180 € per passenger.Departing Tue, 4 Aug, returning Wed, 5 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Tue, 4 Aug, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 5 Aug, arriving in Orlando International.Price includes taxes and charges.From 180 €, select.
Chicago.183 € per passenger.Departing Tue, 29 Sep, returning Tue, 6 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Tue, 29 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 6 Oct, arriving in Orlando International.Price includes taxes and charges.From 183 €, select.
Chicago.184 € per passenger.Departing Thu, 8 Oct, returning Tue, 13 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Thu, 8 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 13 Oct, arriving in Orlando International.Price includes taxes and charges.From 184 €, select.
Chicago.184 € per passenger.Departing Wed, 28 Oct, returning Wed, 4 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Wed, 28 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 4 Nov, arriving in Orlando International.Price includes taxes and charges.From 184 €, select.
Chicago.186 € per passenger.Departing Wed, 22 Jul, returning Sat, 25 Jul.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Wed, 22 Jul, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 25 Jul, arriving in Orlando International.Price includes taxes and charges.From 186 €, select.
Chicago.189 € per passenger.Departing Sat, 31 Oct, returning Tue, 3 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Orlando International on Sat, 31 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 3 Nov, arriving in Orlando International.Price includes taxes and charges.From 189 €, select.
Chicago.189 € per passenger.Departing Tue, 15 Sep, returning Wed, 16 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Orlando International on Tue, 15 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 16 Sep, arriving in Orlando International.Price includes taxes and charges.From 189 €, select.
Chicago.189 € per passenger.Departing Tue, 4 Aug, returning Tue, 11 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Orlando International on Tue, 4 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 11 Aug, arriving in Orlando International.Price includes taxes and charges.From 189 €, select.
Chicago.190 € per passenger.Departing Wed, 22 Jul, returning Wed, 29 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Orlando International on Wed, 22 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 29 Jul, arriving in Orlando International.Price includes taxes and charges.From 190 €, select.
Chicago.190 € per passenger.Departing Tue, 6 Oct, returning Tue, 13 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Orlando International on Tue, 6 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 13 Oct, arriving in Orlando International.Price includes taxes and charges.From 190 €, select.
Chicago.190 € per passenger.Departing Wed, 4 Nov, returning Sat, 7 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Orlando International on Wed, 4 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 7 Nov, arriving in Orlando International.Price includes taxes and charges.From 190 €, select.
Chicago.192 € per passenger.Departing Tue, 28 Jul, returning Tue, 4 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Tue, 28 Jul, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 4 Aug, arriving in Orlando International.Price includes taxes and charges.From 192 €, select.
Chicago.194 € per passenger.Departing Wed, 29 Jul, returning Mon, 10 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Orlando International on Wed, 29 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 10 Aug, arriving in Orlando International.Price includes taxes and charges.From 194 €, select.
Chicago.194 € per passenger.Departing Wed, 30 Sep, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Orlando International on Wed, 30 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 1 Oct, arriving in Orlando International.Price includes taxes and charges.From 194 €, select.
Chicago.194 € per passenger.Departing Tue, 1 Dec, returning Tue, 8 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Orlando International on Tue, 1 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 8 Dec, arriving in Orlando International.Price includes taxes and charges.From 194 €, select.

Find the cheapest month to fly from Orlando to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Orlando to Chicago Midway flights are currently cheapest in September.
Jul
from 186 €
Aug
from 180 €
Sep
from 175 €
Oct
from 184 €
Nov
from 190 €
Dec
from 194 €
Jan
from 284 €
Feb
from 269 €
Mar
from 278 €
Apr
from 315 €
May
from 278 €
Jun
Find prices

Direct flights from Orlando to Chicago Midway

Orlando to Chicago Midway: Alternative routes

Compare routes from Orlando to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

14km from central Chicago
Closest
from 175 €
Search flights

Chicago O'Hare International

25km from central Chicago
from 94 €
Search flights

Chicago Rockford

127km from central Chicago
Cheapest
from 78 €
Search flights

Orlando to Chicago: Flight information

The things to know before you go.
Cheapest flight found175 €
Cheapest month to flySeptember
Average flight time2 hrs, 52 mins
Most popular airlineSouthwest Airlines
Average flights per week48

Finding cheap flights from Orlando to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Orlando to Chicago Midway is 175 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 52 minutes is the average flight time from Orlando to Chicago Midway.
Southwest Airlines flies direct from Orlando to Chicago Midway.
As of July 2026, there are 48 flights per week flying from Orlando to Chicago Midway.
The cheapest month to fly from Orlando to Chicago Midway is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Orlando to Chicago Midway Airport on Saturday, 5 September 2026.
Yes – the average flight time is 2 hours and 52 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Flying from Orlando to Chicago Midway International Airport (MDW): What you need to know

  • Your journey comes together at Orlando's main airport, Orlando International Airport (MCO). Explore the options for booking a flight from Orlando to Chicago Midway International Airport (MDW) departing from this base.

  • The average time for a direct Orlando to Chicago Midway International Airport flight is 2 hours 50 minutes.

  • The timezone in Chicago is UTC-6, which is one hour behind Orlando. Chicago Midway International Airport is located in Chicago.

  • With 37 direct flights a week between the two airports, Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) is the busiest route. Frontier Airlines operates the earliest flight at 6am. If you're eager to get more out of your day before you fly, the latest flight from MCO to MDW is with Southwest Airlines at 10:50pm.

  • For hassle-free travel, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This way, you'll have plenty of time to board your flight from Orlando to MDW.

  • March is a popular time to fly out. If you're taking off then or around a major holiday like Christmas, be there even earlier. Aim for at least two hours ahead for domestic flights and as much as four hours for international journeys.

Airports in Orlando

Orlando International Airport (MCO)

  • You can hop on a direct flight from Orlando to Chicago Midway International Airport (MDW) departing from Orlando International Airport (MCO).

  • Book your direct flight from Orlando to Chicago Midway International Airport with Southwest Airlines. This popular airline operates services from MCO.

  • The most frequently booked airline between MCO and MDW is Southwest Airlines.

  • The carrier with the top on-time arrival performance on this route is Frontier Airlines.

  • Located around 19 kilometres from the centre of Orlando, MCO can be reached in about 25 minutes by car (depending on traffic). The journey by public transport takes roughly 1 hour.

  • Want a leisurely start to your break? Stay near Orlando International Airport. Whether you're boarding an early flight from Orlando to Chicago Midway International Airport or just don't like being rushed, these hotels are the answer:

  • Of the flights that depart from Orlando International Airport, 77% arrive on time at their destination.

  • You'll find MCO at One Airport Boulevard.

Orlando Sanford International Airport (SFB)

  • SFB is around 40 kilometres from central Orlando. It takes 35 minutes or so to get to the airport driving from the city centre. Public transport takes roughly 1 hour.

  • Catching the earliest flight? Think about checking in to one of these accommodation options near Orlando Sanford International Airport the day before your Orlando to MDW flight:

  • 69% of flights taking off from Orlando Sanford International Airport stick to their scheduled arrival time.

About Chicago Midway International Airport (MDW)

  • If you're coming in on a late flight from Orlando to Chicago Midway International Airport, nothing beats the convenience of staying close to the terminal. Collect your bags from the carousel and then be showered and resting soon after at one of these options near MDW:

  • Booking your vehicle around four weeks ahead of your Orlando to Chicago Midway International Airport flight can help you secure the lowest rate.

  • You'll find MDW at 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • From Chicago Midway International Airport, central Chicago is around 16 kilometres away. It takes about 25 minutes to get to the city centre by car.

  • Travelling on public transport will take you around 30 minutes.

How to find the cheapest flights from Orlando to Chicago Midway International Airport (MDW)

  • At the moment, 81 € is the best price we've found for a one-way ticket from Orlando to Chicago Midway International Airport. The cheapest price for a return flight is 175 €. Remember fares can change due to availability at the time of booking.

  • Don't leave everything to the last minute. You're more likely to find cheap flights from Orlando to MDW if you book ahead. Airlines often offer some great early bird discounts.

  • The 'Whole month' search tool will show you the cheapest Orlando to Chicago Midway International Airport tickets throughout the month. It's a good way to find a bargain if your plans are flexible.

  • You don't need to check back in every day to find out if fares have dropped when you set up a Price Alert. We'll let you know when a lower fare pops up on plane tickets from Orlando to MDW.

  • Tailor your flights using filters. Pick your departure and arrival times, airlines and total journey duration. You can also sort the results by 'Best,' 'Fastest' or 'Cheapest' flights from Orlando to Chicago Midway International Airport.

The best time to fly from Orlando to Chicago Midway International Airport (MDW)

  • Think about your travel style when picking your flight dates. November is the quietest month to visit Chicago. July is when most people book flights from Orlando to Chicago Midway International Airport (MDW), which may be ideal if you're chasing more excitement.

  • The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Book your Orlando to MDW plane ticket then if this is the type of weather you enjoy.

  • For cooler conditions, search for a cheap ticket from Orlando to Chicago Midway International Airport in January when temperatures are between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of the United States

  • You've visited Chicago, now it's time to discover more of the United States. Travel around 257 kilometres southeast to Indianapolis to tick off its top sights. From Lucas Oil Stadium to Eiteljorg Museum and The Children's Museum of Indianapolis, your itinerary will be busy.

  • If you're eager to discover another corner of the United States, head for Milwaukee, about 137 kilometres north of Chicago. Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo are among the biggest draws.

Plan the rest of your trip from Orlando to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.