CHI - SWF

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Sat 3/11

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Good to know

Low season

February

High season

April

Cheapest flight

$66

Average price round-trip

$281

Good deal round-trip

$227

Good deal one-way

$2,782
Best time to beat the crowds with an average 47% drop in price.
Most popular time to fly with an average 36% increase in price.
Flight from Chicago to New Windsor Stewart
(avg. price over the last 2 weeks)
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When to book flights from Chicago to Stewart

Estimated round-trip price
Average price per month
Flight prices as travel date approaches

Top tips for finding a cheap flight out of Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $2,782 or less one-way and $227 or less round-trip.
  • High season is considered to be March, April and May. The cheapest month to fly is February.
  • Morning departure is around 1% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking flights from Chicago to Stewart Intl.

Top airlines flying Chicago to New Windsor Stewart

Scores according to KAYAK customer reviews
7.2
Allegiant AirOverall score based on 1988 reviews
7.7Boarding
7.0Comfort
8.1Crew
6.1Entertainment
6.3Food
Airline reviews
Pros: "Crew was good but baggage claim took forever. The seating was not well arranged. The seats were very uncomfortable. The weight limit of the bags were unreasonable"
Cons: "Better seats could be better"
Read more about Allegiant Air
Pros: "Crew was good but baggage claim took forever. The seating was not well arranged. The seats were very uncomfortable. The weight limit of the bags were unreasonable"
Cons: "Better seats could be better"
Pros: "Great crew. Everything was on time. Loved it"
Cons: "Major delays, no communication from airline"
Cons: "Seats are uncomfortable"
Pros: "Nothing really"
Cons: "Depart on time Not Loose my luggage Track all luggage every step of the way instead of crisis management only when a lost luggage claim is filed"
Pros: "Friendly crew."
Pros: "The boarding was quick and efficient, the plane was really clean."
Cons: "It would be nice to be able to recline the seat, and if at least water was served (even if snacks and other drinks cost money)."
Cons: "Seats are uncomfortable after about 40 minutes. Very cramped."
Pros: "Allegiant is a Budget airline. Good fares and great service. Nonstop service to less traveled destinations"
Cons: "Nothing for the price."
Pros: "The actual flight was comfortable and the crew was good."
Cons: "Flight time was pushed back a few weeks ago. Slow boarding process so we landed about 30 min late."
Pros: "Nice pilot and crew."
Cons: "The warning about alcohol was a bit sarcastic, but I guess in today's world people who have acted out are the real culprits..."
Pros: "The plane, the crew..."
Cons: "Seats wider"
Pros: "Nothing"
Cons: "Super rude personelle"
Cons: "It was to uncomfortable to sit there in the plane for so long. I also noticed one of the flight attendants with the long brunette hair kept over looking me but would be in all the guys faces instead. Pretty sure it was a jelouse thing. The shorter brunette girl was really pleasant"
Pros: "Friendly pilot."
Cons: "My reading light kept flashing off and on. So I couldn't read my book."
Cons: "I bought a flight that I had to end up cancelling - when I called to cancel - within the 24 hour period, they would not let me cancel despite text on my confirmation saying that there would be a free cancellation within the 24 hours. Extremely annoyed that there was a blatant miscommunication. I did not end up going on the flight but was unable to get a refund which seems ridiculous given that there was text on the website explicitly saying this was their policy."
Pros: "Flight crew were friendly and courteous and even added some humor. Flight was on time for departure and 20 min early on arrival. Couldn’t beat the fare. Only airline to fly direct non stop to my location."
Cons: "Had to pay for drinks or snacks. Seats did not recline. Fortunately only a little over a 2 hour flight."
Pros: "Easy boarding, very nice crew. I would definitely recommend spending the extra for Priority, it is much faster."
Pros: "That we made it once we were in the air"
Cons: "The 3 hour delay that should have been announced but we had to get alerts on line not from the airline but Kayak"
Cons: "So many charges at every step. $5 for boarding passes?"
Cons: "Extra charges for everything, even water"
Pros: "Flight crew were very polite and we received free soda. Free booze however would have been more appropriate after spending my entire New Year’s Day in an airport."
Cons: "Reviewed 9 hours because a crew member didn’t show. Was originally told 6 hours delay only 20 minutes before the flight was due to leave. Received two $8 meal vouchers and rude and slow service from the entire ground crew."
Cons: "parking my car 2 weeks in Asheville Long term was $96. I should have gone to Charlotte, parked at my friend's house and paid AA the same rate for a nicer seat and cabin leg room. a la carte pricing ran my bill up even with NO checked luggage. Asheville doesn't have a shuttle service for the long-term parking."
Pros: "It got us there and back for a descent price. The flight was fine but the seats are not comfortable and do not recline. I wouldn't suggest Allegiant for anything more than 2 hours and that was even pushing it."
Cons: "We arrived 3.5 hours early and the line was very long. They must have had a system glitch but didn't communicate to anyone in the line as to what was going on. When it did come time to board, they told everyone in the line that was going to Cincinnati that we couldn't check in until 2 hours before the departure time. Apparently there were some other flights that left before us. If they had told us to keep our place in line and to let other people through, that wouldn't have been a problem. But, they didn't. Their own website says you should check baggage at least 2 hours before your flight and no more than 4 hours before. They took it upon themselves to change the rules on people who arrive early. Then, once they no longer had anyone else to check in, they changed their rules again and start checking in people for Cincinnati about 2.5 hours ahead of time. A little communication and brain power from the staff would have gone a long way. After all that mess, the flight was delayed leaving about 15 minutes without any updates from Allegiant either."
Pros: "Flight was on time, the cabin attendants were courteous, and the flight captain kept us informed."
Pros: "I chose this flight knowing it was gonna be a little cramped and no snacks. But I loved the price, so I booked it. The unexpected bonus was the crew. They were down to earth and funny."
Pros: "The price was unbeatable, especially if you don't pay for a checked bag, carry-on, or a soda on the flight. Very smooth flight as well."
Cons: "The plane interior looks like it was gutted, then fitted with hard, plastic seats. No headrests, no privacy for the flight attendants. Everything costs extra."
Pros: "The staff was nice, kind of, but also unprofessional at time."
Cons: "My flights were both fine but the flight from Fresno to Las Vegas was such a disaster! They switched planes so the majority of the people did not have a seat because the plane did not have any B seats. It would have been nice if ANYONE had made that announcement before we boarded to avoid confusion. Also, the fees are ridiculous! Your app is not user friendly at all! Who the hell charges for a carry on bag?! Are you kidding me?! The directions on the app made it sound like the $17 charge was for an additional carry on item, not the allowed one carry on item. So, when we went to check in and I was told I would have to pay $50 for my mother's carry on, it was livid! Also, are you serious with the $5 fee to print a boarding pass? I will NEVER fly with Allegiant Air again. That is absolutely unacceptable. I will say that the staff was pleasant but the airline is inept and inefficient. The reason I will never fly this airline again because of what a rip off the fees are. Allegiant Air, you should be ashamed of yourself."
Pros: "Fare and friendly staff."
Cons: "No wi-fi."
Pros: "Wow so nice to have an economical fare to Baltimore! On time, courteous, uneventful flight. Couldn't ask for more."
Cons: "All good"
Pros: "Mostly the Price! Wonderful Crew Too!"
Cons: "Wish they had flights on Friday and later on Sunday..."
Pros: "Plane was late. 2 years ago it was late and while there at the airport I heard Allgeant routine runs hours late or cancels. 3-4 hours, not an hour. Good thing I dont fly too often"
Pros: "Well, it was a somewhat inexpensive flight out of a convenient terminal."
Cons: "I say somewhat cheap, because by the time they ala carte everything, it's not so cheap anymore. As in no longer cheap enough to justify the bare bones service. The flight attendants are basically candy salespeople. I typically need help putting things in the overhead bin, but the flight attendant actually told me it wasn't her job. That indeed may be the airline's bad policy, but she also thought her way of expressing it was appropriate, which it is not. That has to come straight from the top. Also, what kinda janky airline doesn't serve complementary water. Probably the biggest deal though was that my flight was delayed for 2 hours both ways due to a maintenance issue. I know air travel is fairly safe, but given the track record of both Allegiant and Airbus, I was a little worried during the flights. Even though this particular route is convenient for me, I'm going to avoid Allegiant."
Cons: "Bad service. Long waits. No directions at airport from the airline and counter service slow"
Pros: "The fare"
Cons: "Seats don't recline. There's NOTHING complimentary not even water"
Cons: "The flight got cancelled - trip had to be completely rearranged."
Cons: "Two planes of passengers in gate area delayed takeoff without warning or information."
Pros: "Arrived an hour before flight. Check in took 25 min and tsa 30 minutes. Tried to go through expedite line but agent refused to let me even though flight was leaving in 30 minutes. I have received better treatment in new York airports than here in Myrtle Beach. Who would have thought. There were 3 others that missed the flight. Why would they not just let's be expedited?"
Cons: "See above"
Pros: "Airline was great. Told us right away they were only going to do one drink service so we could order two. Left on time and had no issues. Would definitely fly with them again. Even though you have to pay to check a bag, it's still a better deal than any other airline out there. People need to stop complaining about the extra fees, do you want cheap or not."
Cons: "Nothing. Was exactly what I expected for a $35.00 flight."
Pros: "I liked how friendly the staff were and how everything was done on time."
Pros: "Quick easy flight"
Cons: "Plane was dirty and old. Was nauseated on both flights."
Pros: "Everything"
Cons: "Paying for my carry on bag."
Cons: "The flight from Las Vegas was changed twice"
Pros: "The outbound leg went well except for the very uncomfortable seats that are thinly padded and do not recline. We left on time and arrived on time."
Cons: "The return trip left five hours late due to a faulty plane. I appreciate not using a plane that was mechanically not working. I also appreciate that we did finally leave on the same day we were to leave. The replacement plane was as uncomfortable as the plane used in the first leg of my round trip."
Pros: "Excellent flight! Down side no wi fi connection and no Internet, you must buy all food and drink but hey for cost of the trip worth it!"
Cons: "No internet or wifi"
Pros: "Nothing"
Cons: "Flight was canceled but they keep telling us that in an hour and that hour never came. We are stuck at the airport. We should get upgraded to 1st class"
Pros: "Replace 1 star ratings with na since offered."
Pros: "The plane was nice, staff friendly, and my flight departed and arrived on time! For what I paid for the ticket, I was very scared of what type of plane I would be on but in the end was pleasantly surprised and will use this airline again!"
Cons: "I don't like how fast the prices change and how they charge for every little thing. But then again my ticket was dirt cheap so I can't really complain."
Pros: "I didn't fly out of newburgh because of the nine hour delay I had to reschedule my flight"
Cons: "Every flight has been late or delayed by 1- 5 hours, unacceptable"
Pros: "Better costumer service !"
Cons: "Everything"
Pros: "I like that we boarded and took off quickly"
Cons: "We boarded 50 minutes lates and thus took off late. NONE of the seats recline past row 13. Baggage took 20 minutes to get to baggage claim"
Pros: "Nothing. I had to miss this flight because I wasn't allowed to board my earlier flight."
Cons: "Allow online check-in. Make the process less complicated and confusing. I had to sort through information from two airlines, kayak.com and kiwi.com. too much!"
Pros: "It was a cheap flight and it was on time and all bags came back."
Cons: "The seats suck and there is no inflight entertainment"
Pros: "the bag check people were very friensly"
Cons: "I got to the airport 2 hours before my flight, then waited in line to check my bag for about an hour and 15 minutes. The people at the front said that they were slow because they were short-staffed, and not to worry because the delay was their fault and the plane wouldn’t leave without me. I went straight to the gate, and when I arrived, the gate door was closed. They told me I was too late. They did not have any other flights going out that day—the next one was the following day and was a 30-hour trip, and they said I’d have to pay $100 in processing to switch the flight.They refused to help me book theough another airline. I had to get to my destination that day, so I wound up paying $600 to buy a ticket on another airline. It was the worst traveling experience I’ve ever had."
Pros: "I really like this a-la-carte method- you only pay for what you want. This was an extremely cheap flight ($126RT) and you pay for any upgrades- which we did not require as we travelled with just a backpack for a long weekend to Colorado. The backpack was well within the measurements they allot for the FREE personal item, so we didn’t even have to pay for the carry on as it stowed under the seat in front. The staff was funny and joked over the speakers, they were helpful and smiling."
Cons: "Nothing to complain about. That’s the way to do it, Frontier!"
Pros: "Friendliness, smiles and on time"
Cons: "No complaints"
Pros: "The crew was supper attentive and upbeat."
Cons: "I did not like the delay for 2 and a half hours. But they did hurry to fix the problem."
Cons: "Frontier is a joke. They cancelled the whole trip and left my dad stranded at the airport. F that airlines! Never fly frontier"
Cons: "3 lbs over on luggage wasn’t an issue leaving but return made big deal and said she gets audited and can be a couple of lbs overweight. Wanted $75. So we threw away some liquids and dispersed some closed into carryons. Really stupid. Seats super small uncomfortable always have their hand out for payment for everything. Not eager to fly frontier ever again."
Pros: "No cancellation. No delays. No problems with carry on placement on the aircraft. Good service from the flight attendant."
Cons: "No entertainment. Smaller room space."
Pros: "Price"
Cons: "The line to check bags was the longest line I have ever seen in an airport. There were no lines at any other airline and people were panicking about making their flights. I got to the airport two hours early and I was very close to missing mine. I don’t know what is so different about their process but never again. Also the seats were very close together."
Pros: "Very much Customer Service focused!! From Check-In to boarding to flight to arrival. Very impressive."
Cons: "On both flights, we were 20 minutes early, however, In Denver we had to wait on the tarmac 45 minutes which made us late and in Atlanta, we waited 20 minutes but was on time. You could put a little more padding in the seats. I know it is designed to be as inexpensive as possible but it should not be so uncomfortable. When I fly you again, I will buy one of those items you place around your neck to help you sleep but I am going to sit on it."
Cons: "They charge on carry on bags and seat, need to go on line to book it first, otherwise it charge more on airport. Is not everyone know that. If you missed it, you need to pay much more. By the gate they charge $ 60.00 for carry on. That sick."
Pros: "Fast boarding"
Cons: "Pilot didn't show and he airline gave poor reasons why."
Pros: "extra leg room with seating upgrade"
Cons: "no under seat storage with seating upgrade"
Pros: "Every time I fly frontier, there's always a problem with the plane. This time they have people working in the cabin trying to resolve an issue that is delaying us. It's always something with this airline. I am going to stop flying with them."
Pros: "Friendly crew on the plane"
Cons: "Not very professional employees at the gate. Did not communicate well about our delay"
Pros: "Crew was pleasant"
Cons: "They charge for: a checked bag, a CARRY-ON bag, and your seat choice. There is no on-flight entertainment. The seats don't recline. The check-in counter has massive lines of people and is clearly understaffed. The gate is frequently empty and abandoned with zero people to answer your questions. Flights are late without good reason. Gate agents are understaffed, uninformed, and frazzled. Gate changes were poorly communicated and disorganized. Frontier management and leadership: you should be embarrassed."
Cons: "Three days before christmas on 12-22-16, Frontier cancelled our flight last minute from Phoenix to Cincinnati. I was traveling with two small children. The only option we had to get home was to pay $2200 for 3 one-way Delta tickets. Now I'm in the process of trying to get $1800 dollars back. Frontier initially told me those who bought tickets from another airline could get $600 for every ticket purchased. I have submitted everything requested and now am receiving emails that there is no guarantee I will be reimbursed. Frontier better do what is right and reputable. Customers don't deserve to be treated this way."
Pros: "Frontier seats do not recline."
Cons: "WAITED ON TARMAC ON ARRIVAL IN DENVER 1 HOUR AND WAITED 45 MINUTES AT DENVER FOR THE PLANE TO ARRIVE AND 1 HR IN DENVER FOR THE LUGGAGE TO BE LOADED ON THE PLANE...EVEN THOUGH THE LUGGAGE WAS ON THE CARTS SITTING NEXT TO THE PLANE WAITING TO BE LOADED ONTO THE PLANE."
Pros: "Nothing"
Cons: "CANCELLED frontier flight from punta Gorda. Told me there would be another one in 3 days which is unacceptable. Did not give me any good options and basically told me I was on my own to get home. No notification that flight was cancelled until I arrived at airport and was screwed."
Pros: "the flight crew was awesome. and awesome landing by pilots"
Pros: "The crew was great."
Cons: "It's odd that drinks, even one small cup of soda is a charge. It's one thing to charge for every carry-on/bag, but another for a small can of soda! The cost of the flight appears to be cheap upon booking, but when everything is nickel and dimed it evens out to an airline where you get more amenities."
Pros: "Flight left on time"
Cons: "Paying an extra $80 round trip for luggage - came out to be more expensive than other airlines. Paying for water on the plane is a joke, that used to be free and hydration is important."
Pros: "The crew was very rude, and ignorant, the only thing I did like was that the pilot let us know what was going on"
Cons: "I was the last one on the plane, because I did not check my carry on bag before hand, I was charged 60 dollars. After the fact, I was waiting to get to my seat behind a mom, and her approximately 6 year old son. As I am waiting to find my seat an attendant says to mean, "sir can you please find your seat, we can not back away until you sit down." At this point I am thinking what in the neck do you think it is I am trying to do, but I keep my mouth shut. Then, of course, I have a window seat. So I ask the people in my row to kindly allow me to get into my seat. While an elderly woman is in the process of moving so I can get to my seat, the same attendant says to me in a very demeaning tone "sir please find a seat." Again, I keep my mouth shut, but I am about to lose it on this guy. I finally am moving into my seat, and the attendant announcing over the speaker says, "we can play musical chairs later." I am just disgusted with the way these situations were carried out by the frontier staff. First I pretty much get 60 dollars stolen from me, then I get yelled at and made fun of because I was being kind, and not bashing through people to get to my seat. Not a very pleasant situation, I will never fly frontier again, spirit staff is way nicer, and the prices are cheaper too."
Pros: "The price of the flight... Crew was cool"
Cons: "Paying extra for an emergency exit seat and then on the plane what I paid for was non existant. Pretty shiesty if you ask me. Plane was dirty, wrappers not picked out from seat pockets. Seemed similar to a cattle car"
Pros: "Wow. Talk about ripoff. I had to pay 40 dollars to carry on my own bag. The seats didn't even recline. You had to pay a premium price to get the reclining seats. Crew was nice but made no attempt to help the woman vomiting beside me or the elderly ladies next to me. I felt like they should have paid me the 40 dollars for taking care of there customers. Spend a little extra and ride a different airline. They were the worse."
Pros: "Nothing"
Cons: "Everything"
Pros: "The staff on the flight were very friendly"
Cons: "The takeoff time for the flight seemed to be delayed by people trying to fight over overhead carryon space. There isn't much the airline could do. I spoke with customer service on the phone multiple times on the flight regarding various issues. They were able to help on about half of them. Response time was extremely long and trying to get a hold of someone was nearly impossible (When through a bunch of prompts to discuss issues with a computer instead of a real person. Yes I tried pressing "0" every chance I could to be redirected)"
Pros: "good experience"
Cons: "We sat on the runway for TWO HOURS before they finally decided the plane really was broken and we needed to switch to a new one. We waited another 40 minutes at the new gate for a crew to show up. I thought, since the flight was going to be getting in four hours late, that the crew might even give us a free bag of pretzels or something because that would have made people less irate and would have been than refunding even a single ticket, but nope. All we got was a "don't let the door kick your on the way out" attitude."
Pros: "Space on the plane seemed to comparable or a little better than other airlines."
Cons: "Plane arrived late at gate yet flight schedule was still shown as on time. Check in kiosk did not work so I went to a desk assistant. Desk assistant printed out boarding passes but when I went to board, gate attendant said that I didn't have a seat. I need a system that is much more user friendly (i.e. Southwest). I will probably look for an airline other than frontier next time."
Pros: "Same as above comment"
Cons: "They dont even serve free drinks, took about 35 minutes to bring me water, and were rude."
Pros: "I got one free drink for the delay"
Pros: "Boarding was quick, crew was nice, comfort was okay but for the price it was expected."
Cons: "When I booked the tickets I didn't know there was a charge associated with carry-on luggage. On my phone it was $40, at the check-in it was $45, and at the gate it was $60..."
Cons: "Being delayed 30 min at the gate and then another hour in the air !"
Pros: "The flight crew was fun especially the male flight attendant.Also liked the duration of the flight."
Cons: "No complaints."
Cons: "I didn't realize when I booked how many things Frontier charges you for that are complimentary on other airlines, including carry on luggage and soft"
Pros: "I made it alive"
Cons: "Everything else. We left late (couple hours), the attendents said looking like a 7:15 departure... No update...8:10 departure, ran out of the snack items we wanted, no wifi, uncomfortable chair, no entertainment, arrived but then sat on Tarmac, again attendent said just a few minutes but 25 later we moved to gate just to wait for the crew that wasn't there yet. Seemed really super unorganized and would have been better if they just told us straight up how long it was going to take. Cost me a whole bunch of money. I would have just flown the next day and skipped a night at a hotel, a car rental, taxis and we were so late we didn't even get to eat before bed. Absolutely the worst flight ever. Hard to believe since it is only two hours and I travel a lot! Won't be traveling Frontier again."
Cons: "Late - behind schedule and the online check in wasn't working correctly."
Pros: "Price. Breezed through security! Quiet:)"
Cons: "New seats don't recline and hard to sleep in."
Pros: "nothing"
Cons: "Seats were the most uncomfortable ever. Tray backs were about size of a pack of cheese crackers. Would barely hold a soft drink. At no time during my booking or printing of the itinerary was there any mention that if I chose my own seat there would be a hefty up-charge and that I would be charged $30.00 each way for a carry on bag. They don't tell you this until you've paid the fare and it's time to print the boarding pass. I have no idea how this airline stays in business. By the time I paid all the excess charges I could have flown on Delta on a nice plane with nice seats. Fool me once shame on you. Fool me twice shame on me. Never again will I fly Frontier. I'd rather take the bus."
Pros: "Direct flight"
Pros: "The best asset Frontier has left is an exceptionally friendly and efficient staff. These wonderful people are saving the Frontier experience."
Cons: "The planes have been reconfigured with rigid seats, no leg room and no entertainment - so very different than the Frontier of a decade ago."
Pros: "Nothing. I'll never fly Frontier again"
Cons: "My ticket ended up having 260.00 more dollars added on the back end because of choosing my seat, charging for carry on."
Cons: "Frontier did not disclose their check in 45 mins before take off policy very clearly and I missed my flight as I was there 40 mins before. Frontier customer service was 100% not helpful at the time. I'll do what I can to avoid frontier from now on."
Cons: "Worst seats I've ever been on."

Book cheap flights from Chicago to Stewart Intl.

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2/14Tue
1 stopFrontier
8h 08mMDW-SWF
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$95
3/8Wed
2 stopsMultiple Airlines
20h 04mORD-SWF
$96
2/14Tue
1 stopMultiple Airlines
9h 22mORD-SWF
$98
2/7Tue
1 stopFrontier
26h 22mMDW-SWF
$98
3/21Tue
1 stopMultiple Airlines
11h 53mORD-SWF
$99
2/14Tue
1 stopFrontier
26h 22mMDW-SWF
$99
3/3Fri
2 stopsAllegiant Air
23h 26mMDW-SWF
$141

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Flights to Stewart Intl.

Destination:

Stewart Intl. (SWF)United States

Return flight deals:

Stewart Intl. - Chicago

Cabin classes:

$166