United's Economy Plus offers up to 6 inches more legroom than standard economy seats.
United's Priority Boarding places you in Zone 2, reducing carry-on gate-check risk.

Planning a trip from Chicago to New York? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.
When booking a flight from Chicago to New York, it's generally cheapest to fly on a Tuesday in February. This could help you save money on your trip.
Day of Week: Choose to fly on a Tuesday for the cheapest fares.
Booking Advance: Book your flight at least 180 days in advance to get the best deal.
Cheapest Airline: Consider flying with Spirit Airlines, which generally offers the cheapest fares.
Route Selection: The route from Chicago O'Hare (ORD) to New York LaGuardia (LGA) is typically the cheapest.
Direct or Layover: It's cheaper to fly direct, despite common misconceptions.
AI-powered; AI can make mistakes.
| Low season | February |
|---|---|
| High season | December |
| Cheapest flight | $46 |
Direct departures
Chicago to New York
Monday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Tuesday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Wednesday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Thursday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Friday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Saturday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Sunday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Direct returns
New York to Chicago
Monday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Tuesday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Wednesday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Thursday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Friday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Saturday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Sunday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!
Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!
No delays and arrived to destination 30 min early. Staff was super friendly.
San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.
It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.
Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight
Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.
Everything a cheap airline should be at normal airline rates.
Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.
Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.
Full cans of soda would be nice. A choice between two snacks would be appreciated.
I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!
Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!
One of the best airlines that I flew on, the flight attendants were very attentive and professional.
The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.
Delta made it easy, comfortable and timely. The crew was fantastic.
On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.
Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!
De planning was an absolute mess. We were never told that we weren’t at the gate and that we had to go down unstable stairs and then hop on a bus. People were falling, we couldn’t tell who was in charge. Overall terrible communication that ended up leaving a bad impression at the very end of the experience.
For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.
My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.
After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.
Very thoughtful flight attendant offered me water immediately since I had run to make my connection.
Always wish for more healthy, gluten free options. We have to bring our own.
Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.
Other than a way way too cold cabinets for the entire flight, all was great
One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.
Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.
I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion
Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!
It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.
RIC Staff was not enough. Elderly passengers had to wait 30 minutes to deplane, so we could board and still had to walk as no chairs were provided. And, passenger in front of my seat assignment rammed seat against my legs entire flight time. Was mildly bruised and left thigh still sore.
Overall, an average flight; food options were not the best, and there were bugs on the plane.
There was no TV's on the plane? I tried to activated the WiFi multiple times before the plane took off but it wasn't work well.
Air Marco’s fleet of airplanes are old and pathetic. The seats are torn and stained. The monitors don’t work properly. If this wasn’t a business trip and I had control of booking the flight, I would not travel on this carrier.
Good service, friendly staff. Food was average for airlines and the seats were small.
Pathetic check in experience once again. Not enough staff scheduled at bag drop or for special assistance at LHR. Really need to rethink the whole self check in procedure. The crew was good. A very decent selection of special meals in this leg as compared to the JFK-LHR leg.
Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!
Overall fine, but the delay was annoying and the reasons for the delay were not communicated. The crew on board were phenomenal!
A cookie and a soda, packed like sardines, will never be a positive experience. Also, boarded a 5:30 flight at 7:45pm
Whenever a passenger purchase a ticket his advantage number should automatically to his information. It's not everyone remember the number. You request for your number and American airline agent say they will email it....and they never email anything and you loose your mileage just because you don't remember your number. It should automatically go your information and associate with your email account at all times
Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.
Endless, trip oof my life, we still are in in plane waiting for getting off.after 3 hours delay. Not even a glass of water.
My experience was terrible. They cancelled my flight twice. They kept delaying it and leading me on, acting like the flight was going to go when it never had a chance. I missed out on valuable family time because of spirit and I won’t be flying with them again.
Spirit is low fare air line. Food also cost you. No free food.
The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral
Everyone was kind for the most part. I did travel with children and paid for seats and even then it was not as suitable. I tried calling their customer service prior to check in and I was told they couldn't help me because I didn't purchase my tickets with them.
It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.
The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.
Onboarding was an easy process. Staff waa friendly and courteous. Should have a complimentary snack and drink. We paid $900 round trip for two to myrtle from New York, which is an expensive fare. Going to the seats were not in good shape but our return home, the air plane seemed to be new with comfortable seating with slightly more space. If traveling again, we will still consider flying SpIrit.
It was absolutely awesome. The crew was welcoming to all, not just the first class. They were full of energy. The in-cabin music was an excellent choice, not boring like most airlines. We were ready for takeoff ahead of time. Pilots were great. Smooth takeoff and landing. The plane was beautiful and nicely cleaned. This was truly a fantastic flight. I fly Delta and American all the time. I was apprehensive about Spirit. I will definitely be looking for Spirit first. Thanks for a great experience.
| Transportation mode | Average price | Average duration |
|---|---|---|
| Flights | $570 | 2h 04m |
| Buses | $264 | 20h 19m |