$130 Find Cheap Flights from Chicago Midway Airport to New York State - Compare and Save

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Cheap Flights from Midway to New York

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
New York
New York1 stop$260
Buffalo
Buffalo1 stop$248
Albany
Albanynonstop$269
Syracuse
Syracuse1 stop$341
Rochester
Rochesternonstop$299
Ithaca
Ithaca2 stops$564
Binghamton
Binghamton1 stop$547
New York
New York1 stop$260
Buffalo
Buffalo1 stop$248
Albany
Albanynonstop$269
Syracuse
Syracuse1 stop$341
Rochester
Rochesternonstop$299
Ithaca
Ithaca2 stops$564
Binghamton
Binghamton1 stop$547
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to New York State 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 Chicago Midway Airport to New York State recently?

Here are the cheapest round-trip fares from Chicago Midway Airport to New York State on KAYAK in the last week:

• Buffalo (BUF) from $248
• New York LaGuardia (LGA) from $260
• Albany Intl (ALB) from $269

How do fares into airports in New York State compare?

According to KAYAK data from the last 12 months, the cheapest airports to fly into New York State from Chicago Midway Airport are:

• New York LaGuardia (LGA) (avg. price $308)
• Syracuse Hancock Intl (SYR) (avg. price $358)
• Albany Intl (ALB) (avg. price $379)

Are flights from Chicago Midway Airport to New York State cheaper or more expensive than last year?

Fares from Chicago Midway Airport to New York State are about 152% higher than they were in November last year, averaging $499 round-trip.

What's the cheapest month to fly from Chicago Midway Airport to New York State?

April is typically the cheapest month to fly from Chicago Midway Airport to New York State, with round-trip fares averaging $207. July and October are usually the most expensive, averaging $359 and $353, respectively.

How do fares from Chicago Midway Airport to New York State vary by day of the week?

On average, Tuesday is the cheapest day to fly from Chicago Midway Airport to New York State and Monday is the most expensive. Looking at the past 12 months of KAYAK data, it's 31% more expensive to fly on a Monday compared to Tuesday.

What's the best time of day to fly from Chicago Midway Airport to New York State?

It's cheapest to fly to New York State in the morning with average prices of $269. The afternoon is the most expensive time to fly, with average prices of $369.

What's the best time to book a flight from Chicago Midway Airport to New York State?

Book your flights 7 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 46% compared to booking at the last minute (within 2 weeks of departure).

Key details for Chicago Midway Airport to New York State flights

Low season

February

Cheapest flight

$130
Beat the crowds with an average 28% drop in travelers.
The most popular month to fly with an average 35% increase in travelers.
One-way flight from Chicago Midway Airport to Albany

Your Chicago Midway Airport to New York State 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 Chicago Midway Airport to New York State?

    Fares from Chicago Midway Airport to New York State are around their usual level right now. A round-trip under $192 is considered a good deal, so it's worth keeping an eye out, or setting a Price Alert to catch fare changes.

  • How much should I budget for a flight from Chicago Midway Airport to New York State?

    Over the past 12 months, round-trip fares from Chicago Midway Airport to New York State have typically cost between $192 and $398.

  • What are the main airports serving New York State?

    New York State has 24 airports. 78% of KAYAK users choose New York LaGuardia (LGA) as their arrival airport.

  • Which airlines fly nonstop from Chicago Midway Airport to New York State?

    Based on the flight schedule for the next 3 months, just one airline regularly flies nonstop from Chicago Midway Airport to New York State: Southwest.

  • Which destinations in New York State can I fly nonstop from Chicago Midway Airport?

    Based on the flight schedule for the next 3 months, you can fly nonstop from Chicago Midway Airport to 4 destinations in New York State. The most popular among KAYAK travelers are New York, Albany and Buffalo.

  • Is it cheaper to fly with a layover from Chicago Midway Airport to New York State?

    No, nonstop flights from Chicago Midway Airport to New York State are typically the cheaper option, averaging $287 over the past 12 months.

  • How long is a flight from Chicago Midway Airport to New York State?

    Nonstop flights from Chicago Midway Airport to New York State take 1h 55m on average. The fastest scheduled flight takes 1h 25m, flying into Buffalo (BUF).

  • Which cabin classes are available from Chicago Midway Airport to New York State?

    On flights from Chicago Midway Airport to New York State you can book Economy Class, Premium Economy Class or First Class.

  • What are some popular landmarks around New York State?

    New York State is home to many popular sights. KAYAK travelers' favorites include:

    • Times Square
    • New York City Center
    • Madison Square Garden
    • Rockefeller Center

  • What are the earliest and latest flights from Chicago Midway Airport to New York State?

    The earliest nonstop flight from Chicago Midway Airport to New York State departs at 5:00 am and the latest leaves at 8:40 pm. Nonstop flights take about 1h 55m.

Your guide to booking Chicago Midway Airport to New York State flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 7 weeks before your trip. KAYAK data shows fares in this window are around 46% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • Flexible with your dates? Fly in April to save some money. It's typically the cheapest month on this route, while flights in July will cost you the most.
  • Fly out on a Tuesday to get the cheapest fares. Avoid Monday flights, which are about 31% more expensive.
  • If you're watching your budget, fly into New York LaGuardia (LGA) which has the lowest average airfare in the region. Just remember to budget for any onward travel by bus, car or domestic flight.
  • Start your trip in New York, the most popular destination in New York State. From there, it's easy to continue on to other popular spots such as Brooklyn, Queens and Niagara Falls.
  • Time or money? If speed matters most, fly from Chicago Midway Airport to Buffalo (BUF). If you're after the lowest fares, New York LaGuardia (LGA) is usually your best bet.

Reviews of the top airlines flying from Midway to New York

 
Need help choosing which airline to fly with from Midway to New York? 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 4223 reviews
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

I like the staff members they were super nice and helpful very sweet people :)

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

It good. Just not that plane didn’t have power outlets to charge devices etc.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

More options for your flight from Midway to New York

Complete your trip to New York with a hotel stay or car rental