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Cheap Flights from Orlando Sanford to Chicago Midway

Compare Orlando Sanford 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 Sanford to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Orlando Sanford to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.Rs35,034 per passenger.Departing Sat, 13 Jun.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Orlando Sanford on Sat, 13 Jun, arriving in Chicago Midway.Price includes taxes and charges.From Rs35,034, select.
Chicago.Rs35,822 per passenger.Departing Thu, 28 May.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Orlando Sanford on Thu, 28 May, arriving in Chicago Midway.Price includes taxes and charges.From Rs35,822, select.
Chicago.Rs39,612 per passenger.Departing Sun, 1 Mar.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Orlando Sanford on Sun, 1 Mar, arriving in Chicago Midway.Price includes taxes and charges.From Rs39,612, select.
Chicago.Rs40,080 per passenger.Departing Thu, 26 Feb.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Orlando Sanford on Thu, 26 Feb, arriving in Chicago Midway.Price includes taxes and charges.From Rs40,080, select.
Chicago.Rs44,757 per passenger.Departing Sat, 11 Jul.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Orlando Sanford on Sat, 11 Jul, arriving in Chicago Midway.Price includes taxes and charges.From Rs44,757, select.
Chicago.Rs51,039 per passenger.Departing Thu, 6 Aug.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Orlando Sanford on Thu, 6 Aug, arriving in Chicago Midway.Price includes taxes and charges.From Rs51,039, select.
Chicago.Rs98,469 per passenger.Departing Wed, 1 Apr.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Orlando Sanford on Wed, 1 Apr, arriving in Chicago Midway.Price includes taxes and charges.From Rs98,469, select.

Find the cheapest month to fly from Orlando Sanford to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Orlando Sanford to Chicago Midway flights are currently cheapest in June.
Feb
from Rs40,080
Mar
from Rs39,612
Apr
from Rs98,469
May
from Rs35,822
Jun
from Rs35,034
Jul
from Rs44,757
Aug
from Rs51,039
Sep
Find prices
Oct
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Nov
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Dec
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Jan
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Orlando Sanford to Chicago Midway: Alternative routes

Compare routes from Orlando Sanford 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 Rs35,034
Search flights

Chicago O'Hare International

25km from central Chicago
from Rs34,193
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
Cheapest
from Rs12,471
Search flights

Orlando to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs35,034
Cheapest month to flyJune

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

The best price we found for a return flight from Orlando Sanford to Chicago Midway is Rs89,993. 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.
Currently, there are no airlines that fly direct from Orlando Sanford to Chicago Midway. But we found flights with one or more stops from Rs89,993.
As of February 2026, there are no flights flying from Orlando Sanford to Chicago Midway.
The cheapest month to fly from Orlando Sanford to Chicago Midway is usually June.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Orlando Sanford Airport to Chicago Midway Airport on Saturday, 6 June 2026.
No airlines currently offer direct flights between Orlando Sanford Airport and Chicago Midway Airport. Most routes have one or more stops.
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.
Currently, Allegiant Air offers the cheapest flight tickets to Chicago Midway.

Flying from Orlando Sanford International Airport (SFB) to Chicago Midway International Airport (MDW): what you need to know

  • The timezone in Chicago is UTC-5, which is one hour behind Orlando.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are travel rules worth sticking to. Show up at the airport on time to board your SFB to MDW flight.

  • Flying during a peak time like July? Major public holidays and other popular periods can lead to longer queues at check-in and security. Play it safe and arrive up to four hours ahead of international flights and two hours before domestic departures.

  • We make it simple to book a flight with a stopover. To see all your options for tickets from Orlando Sanford International Airport to Chicago Midway International Airport, deselect 'Direct flights only.' Then, pick a flight offering a stop long enough to tour your chosen city. Some great stopovers between SFB and MDW include:

    • Asheville Regional Airport

    • Nashville International Airport

    • Gerald R. Ford International Airport

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

  • The lowest price we've seen for a one-way Orlando Sanford International Airport to Chicago Midway International Airport flight is Rs35,034. A round-trip ticket is currently Rs89,993. Depending on the availability when you book, these fares could change.

  • To find cheap tickets from SFB to MDW, book ahead. Airlines typically offer lower fares when flights are first made available.

  • Finding cheap flights from Orlando Sanford International Airport to Chicago Midway International Airport is more likely if you're flexible with your dates. Use the 'Whole month' function to see the lowest fares throughout the month and land a great deal.

  • Spend less time searching for cheap flights from SFB to MDW by setting up a Price Alert. You'll get an email or notification through the app when a lower fare pops up.

  • Lock in the ideal flight for you with the help of the filters. To see the 'Fastest,' 'Cheapest' or 'Best' flights from Orlando Sanford International Airport to Chicago Midway International Airport, use the 'Sort by' function. You can also filter by departure and arrival times, airline, and journey duration.

Handy information about Orlando Sanford International Airport (SFB)

  • Of the flights that depart from Orlando Sanford International Airport, 69.11% arrive as scheduled at their destination.

  • Orlando Sanford International Airport is around 48 kilometres from central Orlando. If you're driving, ride-sharing or catching a cab from the centre, it'll take you 35 minutes or so to get there, depending on the traffic.

  • The trip on public transport takes about 2 hours 5 minutes.

  • Get your journey off to a relaxed start by staying near SFB. Whether you've booked an early flight from Orlando Sanford International Airport to Chicago Midway International Airport or just don't want to be rushed, these hotels have you covered:

Arriving at Chicago Midway International Airport (MDW)

  • The last thing you need is a lengthy journey to your hotel if you're arriving on a late Orlando Sanford International Airport to Chicago Midway International Airport flight. Reserve one of these accommodation options near MDW instead:

  • Go wherever you want, whenever you want with a Chicago Midway International Airport rental car. Pick up your wheels from Dollar, Hertz or Budget and discover more of Chicago and beyond.

  • Secure the lowest price by booking your ride from Chicago Midway International Airport around four weeks before your travel date.

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

  • The address for MDW is 5700 South Cicero.

  • Chicago Midway International Airport is roughly 19 kilometres from central Chicago. Driving there takes about 20 minutes.

  • If you're using public transport, expect a journey of roughly 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • It's time to work out your trip dates for your flight from Orlando Sanford International Airport to Chicago Midway International Airport. July is the busiest month to head to Chicago. If you'd like a quieter vibe, go in May.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC and 29ºC. Book your flights from Orlando Sanford International Airport to Chicago Midway International Airport in this month if you like this kind of weather.

  • If you'd rather travel in cooler conditions, search for a cheap ticket from SFB to MDW in January. Temperatures average between -12ºC and 3ºC then.

Explore more of United States

  • You've seen Chicago, now it's time to discover more of United States. Travel around 451 kilometres south-east to Columbus to tick off its top sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you'll have a packed itinerary ahead.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. No visit is complete without checking out The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Orlando to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.