Cheap flights from Chicago Midway to Islip

Compare Chicago Midway to Islip flight deals

Find the cheapest month or even day of the year to fly to Islip

Book the best Islip fare with no extra fees

Flight deals from Chicago Midway to Islip

Looking for a cheap last-minute deal or the best round-trip flight from Chicago Midway Airport to Islip Airport? If you want to travel next month, round-trip fares start from $378. Find the lowest prices on one-way and round-trip tickets right here.

Find the cheapest month to fly from Chicago Midway to Islip

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Islip flights are currently cheapest in July.

Chicago to Islip: Flight information

The things to know before you go.
Cheapest flight found$378
Cheapest month to flyJuly

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

The best price we found for a round-trip flight from Chicago Midway to Islip is $378. 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 Chicago Midway to Islip. But we found flights with one or more stops from $378.
There are no flights flying from Chicago Midway to Islip, as of June 2026.
The cheapest month to fly from Chicago Midway to Islip is usually July.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Islip Airport on Thursday, July 9, 2026.
No airlines currently offer direct flights between Chicago Midway Airport and Islip 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 Islip 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 Islip is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Islip.

Traveling from Chicago Midway Airport (MDW) to Islip Airport (ISP): what you need to know

  • Give yourself enough time to catch your MDW to ISP flight. It's generally best to arrive two hours before international departures and an hour ahead for domestic flights.

  • During popular months like July, it's best to get to the airport earlier than normal. Plan to arrive two hours before domestic departures and four hours ahead of international flights whenever you're flying during a high season in general.

  • We make it easy to book a flight with a stopover. To see your options for tickets from Chicago Midway Airport to Islip Airport, deselect 'Direct flights only.' Then, choose a flight offering a stop long enough to explore your chosen city. Worthwhile stopovers between MDW and ISP include:

    • Atlanta Hartsfield-Jackson Airport

    • Baltimore Washington International Airport

    • Raleigh / Durham Airport

How to find the cheapest flights from Chicago Midway Airport (MDW) to Islip Airport (ISP)

  • Currently, $133 is the cheapest price we've found for a one-way Chicago Midway Airport to Islip Airport flight. The best price for a return plane ticket is $378. Bear in mind that fares may change due to availability at the time of booking.

  • It's often best to book early if you're looking for cheap tickets from MDW to ISP. That's because flight prices are based on demand, which tends to increase closer to the date of departure.

  • Getting cheap flights from Chicago Midway Airport to Islip Airport is easy if you can be flexible with your travel plans. Use the 'Whole month' search tool to see the lowest prices across every month and land a great deal.

  • Stay on top of deals for cheap flights from MDW to ISP by creating a Price Alert. You'll get an email or notification on the app when a lower fare pops up.

  • Pick your ideal departure and arrival times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to get the best deals on flights from Chicago Midway Airport to Islip Airport.

Handy information about Chicago Midway Airport (MDW)

  • The address for MDW is 5700 South Cicero.

  • When it comes to the on-time performance of Chicago Midway Airport, 76% of flights arrive within the scheduled timeframe.

  • Chicago Midway Airport is around 16 kilometers from central Chicago. If you're ride-sharing, catching a cab or driving from the center, it'll take you 25 minutes or so to arrive, depending on the traffic.

  • Expect a journey time of about 30 minutes on public transport.

  • Need a convenient hotel near MDW? If you're catching an early flight from Chicago Midway Airport to Islip Airport, these accommodation options will put you moments from your departure lounge:

Arriving at Islip Airport (ISP)

Getting from Islip Airport (ISP) to central Islip

  • ISP is located at 100 Arrivals Avenue.

  • Islip Airport is approximately 6 kilometers from central Islip. Driving there takes about 10 minutes.

  • When traveling by public transport, expect a journey time of around 30 minutes.

When to fly to Islip Airport (ISP)

  • It's time to pick your trip dates for your flight from Chicago Midway Airport to Islip Airport. July is the busiest month to visit Islip. If you prefer a more low-key vibe, go in December.

  • Book your flight from Chicago Midway Airport to Islip Airport for July if you want to visit Islip during its warmest month. You can expect temperatures of between 19ºC (66ºF) and 29ºC (84ºF).

  • Look for cheap tickets from MDW to ISP in January if you like traveling in cooler conditions. Temperatures are at their lowest around then, ranging between -4ºC (25ºF) and 8ºC (46ºF) on average.

Explore more of the United States

  • New York is just one of the many cities in the United States waiting to be explored once you've seen Islip. Around 64 kilometers away to the west, its best attractions include Central Park, Statue of Liberty and Metropolitan Museum of Art.

  • If you're interested in discovering another major stop in the United States, head for Philadelphia, about 193 kilometers south-west of Islip. Independence Hall, Liberty Bell and Philadelphia Museum of Art are the start of reasons to visit.

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