$145 Find Cheap Flights from Islip to Illinois - Compare and Save

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Cheap Flights from Islip to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Chicago
Chicago
4h 35m2 stops
from $252per person
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Book Cheap Islip to Illinois Plane Tickets

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Islip to Illinois

Mon, Jan 4 - Wed, Jan 13
Frontier Logo
11:26 am - 1:08 amISP  Islip Long Island-ORD Chicago O'Hare Intl
14h 42m1 stop Orlando
Frontier Logo
5:16 pm - 5:26 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
23h 10m1 stop Orlando
$252Frontier
Sun, Dec 6 - Thu, Dec 10
Frontier Logo
6:10 pm - 1:08 amISP  Islip Long Island-ORD Chicago O'Hare Intl
7h 58m1 stop Orlando
Frontier Logo
5:35 am - 5:30 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
10h 55m1 stop Orlando
$290Frontier
Mon, Nov 30 - Thu, Dec 3
Frontier Logo
4:40 pm - 12:43 amISP  Islip Long Island-ORD Chicago O'Hare Intl
9h 03m1 stop Orlando
Frontier Logo
5:35 am - 1:22 pmORD  Chicago O'Hare Intl-ISP Islip Long Island
6h 47m1 stop Orlando
$330Frontier
Fri, Dec 18 - Tue, Dec 22
Frontier Logo
11:26 am - 7:30 pmISP  Islip Long Island-MDW Chicago Midway
9h 04m1 stop Orlando
Frontier Logo
8:35 pm - 10:31 amMDW  Chicago Midway-ISP Islip Long Island
12h 56m1 stop Orlando
$370Frontier
Fri, Dec 18 - Sun, Dec 20
Frontier Logo
11:26 am - 7:30 pmISP  Islip Long Island-MDW Chicago Midway
9h 04m1 stop Orlando
Frontier Logo
8:35 pm - 10:31 amMDW  Chicago Midway-ISP Islip Long Island
12h 56m1 stop Orlando
$385Frontier
Mon, Jan 4 - Wed, Jan 13
Southwest Logo
5:40 pm - 11:10 pmISP  Islip Long Island-MDW Chicago Midway
6h 30m1 stop Baltimore/Washington
Southwest Logo
6:35 am - 11:50 amMDW  Chicago Midway-ISP Islip Long Island
4h 15m1 stop Baltimore/Washington
$393Southwest
Mon, Jan 4 - Wed, Jan 13
Southwest Logo
12:25 pm - 4:00 pmISP  Islip Long Island-MDW Chicago Midway
4h 35m1 stop Baltimore/Washington
Southwest Logo
1:30 pm - 9:35 pmMDW  Chicago Midway-ISP Islip Long Island
7h 05m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington
$398Southwest
Mon, Jan 4 - Wed, Jan 13
Southwest Logo
5:40 pm - 10:45 pmISP  Islip Long Island-MDW Chicago Midway
6h 05m2 stops Baltimore/Washington Lambert-St Louis
Southwest Logo
8:15 am - 3:45 pmMDW  Chicago Midway-ISP Islip Long Island
6h 30m2 stops Greater Rochester Intl Baltimore/Washington
$403Southwest
Fri, Dec 18 - Tue, Dec 22
Southwest Logo
4:55 pm - 11:15 pmISP  Islip Long Island-MDW Chicago Midway
7h 20m1 stop Baltimore/Washington
Southwest Logo
3:05 pm - 11:50 pmMDW  Chicago Midway-ISP Islip Long Island
7h 45m2 stops Nashville Intl Baltimore/Washington
$418Southwest
Fri, Dec 18 - Tue, Dec 22
Southwest Logo
5:40 am - 12:25 pmISP  Islip Long Island-MDW Chicago Midway
7h 45m2 stops Orlando Columbus
Southwest Logo
3:05 pm - 11:50 pmMDW  Chicago Midway-ISP Islip Long Island
7h 45m2 stops Nashville Intl Baltimore/Washington
$423Southwest
Booking Insights

Price, demand and travel trends for Islip to Illinois flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Islip to Illinois recently?

The cheapest fares from Islip to Illinois on KAYAK in the last week were to Chicago O'Hare Intl (ORD) from $252 round-trip and to Chicago Midway (MDW) from $370 round-trip.

How do fares into airports in Illinois compare?

Flights from Islip to Illinois arrive at a single airport, Chicago Midway (MDW). Round-trip fares average about $386.

What's the best time of day to fly from Islip to Illinois?

It's cheapest to fly to Illinois in the morning with average prices of $358. The evening is the most expensive time to fly, with average prices of $462.

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Key details for Islip to Illinois flights

Low season

January

Cheapest flight

$145
Beat the crowds with an average 74% drop in travelers.
The most popular month to fly with an average 28% increase in travelers.
One-way flight from Islip to Chicago Midway Airport

Your Islip to Illinois flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Islip to Illinois?

    Yes. Fares from Islip to Illinois are low right now. As a rule of thumb, a round-trip under $370 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Islip to Illinois?

    Over the past 12 months, round-trip fares from Islip to Illinois have typically cost between $370 and $443.

  • What are the main airports serving Illinois?

    Illinois has 17 airports. 100% of KAYAK users choose Chicago Midway (MDW) as their arrival airport.

  • Which airlines fly nonstop from Islip to Illinois?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Islip to Illinois. However, Southwest offers a one-stop option.

  • Which destinations in Illinois can I fly nonstop from Islip?

    Based on the flight schedule for the next 3 months, there are no nonstop flights from Islip to Illinois. The most popular destination you can reach with one stop is Chicago.

  • Which cabin classes are available from Islip to Illinois?

    On flights from Islip to Illinois you can only book Economy Class.

  • What are some popular landmarks around Illinois?

    Illinois is home to many popular sights. KAYAK travelers' favorites include:

    • Magnificent Mile
    • Grant Park
    • Soldier Field
    • River North

Your guide to booking Islip to Illinois flights

Get tips on when to book, when to fly and what to know before your trip.
  • Flexible with your dates? Fly in September to save some money. It's typically the cheapest month on this route, while flights in March will cost you the most.
  • Fly out on a Tuesday to get the cheapest fares. Avoid Saturday flights, which are about 161% more expensive.
  • Start your trip in Chicago, the most popular destination in Illinois. From there, it's easy to continue on to other popular spots such as Rosemont, Schaumburg and Champaign.

Reviews of the top airline flying from Islip to Illinois

 
Need help choosing which airline to fly with from Islip to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4219 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

2.0 MediocreKevin, Oct 2026
Read more Southwest reviews

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

My bag was damaged and is now missing a wheel. I tried to buy a claim in on the website but it would not accept my confirmation # for submission. Other than that, everything else was good!

More options for your flight from Islip to Illinois

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