Cheap Flights from New York, NY to Chicago, IL from $55

One way Round trip

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On Cheapflightsplus.com you will find 32 direct and 214 connecting flights from New York to Chicago. You can compare airfare deals from 12 airlines and multiple travel sites from $55, book and save on cheap plane tickets and last minute offers. Also check out NYC-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip New York to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $55 (one-way), $94 (round-trip).

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Best Flights from New York to Chicago Today

Take a look at the list of non stop flights and flights with layovers from New York to Chicago with the lowest price of $55. The fastest direct flight takes 2h 20m and the fastest connecting – 3h 54m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $55 Find flight	18:30 New York La Guardia	20:00 Chicago O'Hare International	2h 30m	Spirit Airlines	NK1179
from $113 Find flight	14:20 New York La Guardia	15:57 Chicago O'Hare International	2h 37m	United Airlines	UA2360
from $114 Find flight	07:20 New York La Guardia	08:57 Chicago O'Hare International	2h 37m	United Airlines	UA561
from $125 Find flight	20:30 New York La Guardia	22:09 Chicago O'Hare International	2h 39m	United Airlines	UA2181
from $135 Find flight	19:30 New York La Guardia	21:09 Chicago O'Hare International	2h 39m	United Airlines	UA1936
from $135 Find flight	21:30 New York La Guardia	23:09 Chicago O'Hare International	2h 39m	United Airlines	UA2603
from $135 Find flight	17:25 New York La Guardia	19:05 Chicago O'Hare International	2h 40m	United Airlines	UA777
from $214 Find flight	14:39 New York La Guardia	16:26 Chicago O'Hare International	2h 47m	Spirit Airlines	NK2479
from $218 Find flight	11:25 New York La Guardia	13:03 Chicago O'Hare International	2h 38m	United Airlines	UA1660
from $219 Find flight	20:30 New York John F Kennedy Intl	22:28 Chicago O'Hare International	2h 58m	JetBlue	B6405
from $254 Find flight	09:29 New York John F Kennedy Intl	11:18 Chicago O'Hare International	2h 49m	JetBlue	B6905
from $254 Find flight	15:29 New York John F Kennedy Intl	17:40 Chicago O'Hare International	3h 11m	Delta Air Lines Inc.	DL5068
from $291 Find flight	07:25 New York La Guardia	09:04 Chicago O'Hare International	2h 39m	American Airlines	AA392
from $299 Find flight	07:30 New York La Guardia	08:50 Chicago Midway	2h 20m	Southwest Airlines	WN4429
from $114 Find flight	22:55 New York La Guardia	00:32+2 дня Chicago O'Hare International	26h 37m layover 19h 38m - Denver	Frontier Airlines	F93161 F93174
from $124 Find flight	11:30 New York John F Kennedy Intl	22:24 Chicago Midway	11h 54m layover 6h 0m - Tampa	Frontier Airlines	F94057 F93899

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 03, 2025

Flight Schedule New York (New York) to Chicago (Illinois)

Full flight schedule will help you in detecting at what time planes fly from New York to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.

Departure	Flight Details	Flight Duration	Price
07:15 — 08:57	07:15 — 08:57 DL5716 Delta Air Lines Inc. New York — Chicago	2h 42m	Find flight from$350
07:20 — 08:57	07:20 — 08:57 UA561 United Airlines New York — Chicago	2h 37m	Find flight from$114
07:25 — 09:04	07:25 — 09:04 AA392 American Airlines New York — Chicago	2h 39m	Find flight from$291
07:30 — 09:09	07:30 — 09:09 AA4464 American Airlines New York — Chicago	2h 39m	Find flight from$291
07:30 — 08:50	07:30 — 08:50 WN4429 Southwest Airlines New York — Chicago	2h 20m	Find flight from$299
07:55 — 09:51	07:55 — 09:51 DL5272 Delta Air Lines Inc. New York — Chicago	2h 56m	Find flight from$384
09:21 — 11:00	09:21 — 11:00 AA3015 American Airlines New York — Chicago	2h 39m	Find flight from$291
09:29 — 11:18	09:29 — 11:18 B6905 JetBlue New York — Chicago	2h 49m	Find flight from$254
10:45 — 12:21	10:45 — 12:21 DL2810 Delta Air Lines Inc. New York — Chicago	2h 36m	Find flight from$363
10:55 — 12:20	10:55 — 12:20 WN3457 Southwest Airlines New York — Chicago	2h 25m	Find flight from$330
11:00 — 12:50	11:00 — 12:50 DL5017 Delta Air Lines Inc. New York — Chicago	2h 50m	Find flight from$371
11:25 — 13:03	11:25 — 13:03 UA1660 United Airlines New York — Chicago	2h 38m	Find flight from$218
12:20 — 13:40	12:20 — 13:40 WN1704 Southwest Airlines New York — Chicago	2h 20m	Find flight from$513
12:24 — 14:03	12:24 — 14:03 AA2644 American Airlines New York — Chicago	2h 39m	Find flight from$464
13:50 — 15:10	13:50 — 15:10 WN3458 Southwest Airlines New York — Chicago	2h 20m	Find flight from$320
14:00 — 15:45	14:00 — 15:45 AA1166 American Airlines New York — Chicago	2h 45m	Find flight from$291
14:20 — 15:57	14:20 — 15:57 UA2360 United Airlines New York — Chicago	2h 37m	Find flight from$113
14:30 — 16:25	14:30 — 16:25 AA4590 American Airlines New York — Chicago	2h 55m	Find flight from$291
14:39 — 16:26	14:39 — 16:26 NK2479 Spirit Airlines New York — Chicago	2h 47m	Find flight from$214
14:50 — 16:38	14:50 — 16:38 DL962 Delta Air Lines Inc. New York — Chicago	2h 48m	Find flight from$350
15:29 — 17:40	15:29 — 17:40 DL5068 Delta Air Lines Inc. New York — Chicago	3h 11m	Find flight from$254
16:35 — 18:05	16:35 — 18:05 WN3459 Southwest Airlines New York — Chicago	2h 30m	Find flight from$450
17:10 — 19:16	17:10 — 19:16 DL2760 Delta Air Lines Inc. New York — Chicago	3h 6m	Find flight from$350
17:25 — 19:05	17:25 — 19:05 UA777 United Airlines New York — Chicago	2h 40m	Find flight from$135
17:30 — 19:15	17:30 — 19:15 AA4784 American Airlines New York — Chicago	2h 45m	Find flight from$372
18:30 — 20:00	18:30 — 20:00 NK1179 Spirit Airlines New York — Chicago	2h 30m	Find flight from$55
18:30 — 20:10	18:30 — 20:10 UA1289 United Airlines New York — Chicago	2h 40m	Find flight from$135
19:25 — 21:43	19:25 — 21:43 DL5679 Delta Air Lines Inc. New York — Chicago	3h 18m	Find flight from$254
19:30 — 21:09	19:30 — 21:09 UA1936 United Airlines New York — Chicago	2h 39m	Find flight from$135
20:30 — 22:09	20:30 — 22:09 UA2181 United Airlines New York — Chicago	2h 39m	Find flight from$125
20:30 — 22:28	20:30 — 22:28 B6405 JetBlue New York — Chicago	2h 58m	Find flight from$219
21:30 — 23:09	21:30 — 23:09 UA2603 United Airlines New York — Chicago	2h 39m	Find flight from$135
05:45 — 15:43	05:45 — 07:30 NK2401 Spirit Airlines New York — Myrtle Beach 6h 48m stop 14:18 — 15:43 NK2074 Spirit Airlines Myrtle Beach — Chicago	10h 58m including layover	Find flight from$220
05:55 — 16:10	05:55 — 08:43 NK2364 Spirit Airlines New York — Orlando 5h 24m stop 14:07 — 16:10 NK2410 Spirit Airlines Orlando — Chicago	11h 15m including layover	Find flight from$165
06:30 — 13:47	06:30 — 09:11 F93287 Frontier Airlines New York — Atlanta 3h 36m stop 12:47 — 13:47 F92291 Frontier Airlines Atlanta — Chicago	8h 17m including layover	Find flight from$139
06:59 — 15:06	06:59 — 09:59 F94871 Frontier Airlines New York — Orlando 3h 11m stop 13:10 — 15:06 F93853 Frontier Airlines Orlando — Chicago	9h 7m including layover	Find flight from$149
07:22 — 12:29	07:22 — 09:30 DL5080 Delta Air Lines Inc. New York — Detroit 2h 46m stop 12:16 — 12:29 DL3567 Delta Air Lines Inc. Detroit — Chicago	6h 7m including layover	Find flight from$258
08:15 — 16:25	08:15 — 09:40 WN2943 Southwest Airlines New York — Nashville 4h 55m stop 14:35 — 16:25 WN1204 Southwest Airlines Nashville — Chicago	9h 10m including layover	Find flight from$242
08:52 — 19:42	08:52 — 11:36 NK2370 Spirit Airlines New York — Houston 5h 26m stop 17:02 — 19:42 NK2690 Spirit Airlines Houston — Chicago	11h 50m including layover	Find flight from$252
09:00 — 13:47	09:00 — 11:37 F91871 Frontier Airlines New York — Atlanta 1h 10m stop 12:47 — 13:47 F92291 Frontier Airlines Atlanta — Chicago	5h 47m including layover	Find flight from$210
09:59 — 16:10	09:59 — 12:52 NK2801 Spirit Airlines New York — Orlando 1h 15m stop 14:07 — 16:10 NK2410 Spirit Airlines Orlando — Chicago	7h 11m including layover	Find flight from$165
10:25 — 16:52	10:25 — 11:51 UA6108 United Airlines New York — Washington D.C. 3h 48m stop 15:39 — 16:52 UA1057 United Airlines Washington D.C. — Chicago	7h 27m including layover	Find flight from$258
11:04 — 23:59	11:04 — 14:14 NK2374 Spirit Airlines New York — Miami 7h 33m stop 21:47 — 23:59 NK2 Spirit Airlines Miami — Chicago	13h 55m including layover	Find flight from$165
11:30 — 22:24	11:30 — 14:32 F94057 Frontier Airlines New York — Tampa 6h stop 20:32 — 22:24 F93899 Frontier Airlines Tampa — Chicago	11h 54m including layover	Find flight from$124
13:19 — 22:22	09:59 — 12:52 NK2801 Spirit Airlines New York — Orlando 4h 5m stop 20:23 — 22:22 NK2343 Spirit Airlines Orlando — Chicago	10h 3m including layover	Find flight from$165
16:58 — 23:27	16:58 — 19:55 NK2331 Spirit Airlines New York — Orlando 1h 24m stop 21:19 — 23:27 NK1369 Spirit Airlines Orlando — Chicago	7h 29m including layover	Find flight from$260
19:55 — 09:22 +1 day	19:55 — 23:05 NK2388 Spirit Airlines New York — Miami 7h 55m stop 07:00 — 09:22 NK2530 Spirit Airlines Miami — Chicago	14h 27m including layover	Find flight from$165
22:55 — 00:32 +2 days	22:55 — 01:15 F93161 Frontier Airlines New York — Denver 19h 38m stop 20:53 — 00:32 F93174 Frontier Airlines Denver — Chicago	26h 37m including layover	Find flight from$114
22:55 — 00:32 +2 days	22:55 — 01:15 F93161 Frontier Airlines New York — Denver 19h 38m stop 20:53 — 00:32 F93172 Frontier Airlines Denver — Chicago	26h 37m including layover	Find flight from$166
15:28 — 16:10 +1 day	15:28 — 17:09 NK2215 Spirit Airlines New York — Columbus 1h 25m stop 18:34 — 20:56 NK2216 Spirit Airlines Columbus — Orlando 17h 11m stop 14:07 — 16:10 NK2410 Spirit Airlines Orlando — Chicago	25h 42m including layover	Find flight from$163
15:28 — 22:22 +1 day	15:28 — 17:09 NK2215 Spirit Airlines New York — Columbus 1h 25m stop 18:34 — 20:56 NK2216 Spirit Airlines Columbus — Orlando 23h 27m stop 20:23 — 22:22 NK2343 Spirit Airlines Orlando — Chicago	31h 54m including layover	Find flight from$163

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on September 3, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from New York to Chicago depends on and how to choose the most interesting flight option for you.

Distance between New York and Chicago is 1144 miles. Time difference between the cities is 1h. Airplanes depart 02:10 to 23:50 from 16 New York airports and arrive 02:10 to 23:50 to 7 Chicago airports. Average flight time is 2h 39m.

The fastest flight 2h 20m
Average flight time 2h 39m
The earliest flight 02:10
The latest flight 23:50
Distance 711 ml

The cheapest months to travel to Chicago are july (from 55 $), august (from 70 $), october (from 113 $).

The most expensive months are june (from 125 $), may (from 114 $), september (from 113 $).

What is the lowest airfare New York to Chicago?

The cheapest plane ticket found by our users is $55. This airfare is for economy class on one-way NK1179 flight by Spirit Airlines for August 9, 2025 which leaves La Guardia in New York at 18:30 am and arrives at Chicago O'Hare International at 20:00.

Economy class

$55

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Business class

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First class

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Popular Airlines on the Route

The flight New York — Chicago is served by 12 regular airlines and 5 low-cost airlines. Most of the flights on this route are operated by JetBlue - 3 departures per week at the price of from $ 219 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 5163.

Direct flights

There are 32 nonstop flights on the route. The fastest direct flight is WN4429 by Southwest Airlines takes 2h 20m and the cheapest is NK1179 by Spirit Airlines for $55.

B6 - JetBlue

from $219

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WN - Southwest Airlines

from $299

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DL - Delta Air Lines Inc.

from $254

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UA - United Airlines

from $113

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NK - Spirit Airlines

from $55

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AA - American Airlines

from $291

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See more direct flights

Connecting Flights

There are 214 flights with layovers on the route. The fastest connecting flight is DL5080 by Delta Air Lines Inc. takes 3h 54m and the cheapest is NK1179 by Spirit Airlines for $114.

B6 - JetBlue

from $519

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WN - Southwest Airlines

from $237

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DL - Delta Air Lines Inc.

from $258

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UA - United Airlines

from $246

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NK - Spirit Airlines

from $163

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AA - American Airlines

from $262

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AS - Alaska Airlines

from $781

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F9 - Frontier Airlines

from $114

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FI - Icelandair

from $1231

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LA - LAN Airlines

from $1869

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SY - Sun Country Airlines

from $364

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AM - Aeromexico

from $1308

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See more connecting flights

Airports

You can fly from New York to Chicago from 16 airports (39th Street Ferry, Newyork Airport, Newyork Airport, La Guardia, Westchester County, World Trade Center, Pier 11/Wall St. SPB, John F Kennedy Intl, Flushing, East 34th St Heliport, West 30th St Heliport, Downtown Manhattan H/p, East 60th Street H/P, Battery Pk City/N. Cov, East 34th St Landing, Marine Air Terminal).

New York airports

39th Street Ferry-XNY

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Newyork Airport-NWK

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Newyork Airport-NYP

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La Guardia-LGA

from $55
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Westchester County-HPN

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World Trade Center-WTC

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Pier 11/Wall St. SPB-NWS

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John F Kennedy Intl-JFK

from $124
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Flushing-FLU

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East 34th St Heliport-TSS

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West 30th St Heliport-JRA

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Downtown Manhattan H/p-JRB

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East 60th Street H/P-JRE

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Battery Pk City/N. Cov-NBP

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East 34th St Landing-NES

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Marine Air Terminal-QNY

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Chicago airports

O'Hare International-ORD

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Midway-MDW

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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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Airplanes

There are flights to Chicago from New York by 12 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.

Airbus A318/319/320/321

from $166

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Boeing 737 MAX 8

from $237

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Boeing 737-100/200

from $246

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Canadair Regional Jet 900

from $254

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Embraer 175 (short wing)

from $254

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Airbus A321

from $262

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Airbus A319

from $272

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Boeing 767

from $272

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Airbus A320

from $281

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Boeing 737-800

from $292

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Top Domestic Destinations from New York

You may also consider searching for discounted plane tickets to some other popular places from New York within United States.

New York — Miami

from $21

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New York — Los Angeles

from $438

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New York — Orlando

from $32

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New York — Boston

from $106

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New York — Atlanta

from $79

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New York — Dallas

from $78

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New York — Chicago

from $32

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New York — Houston

from $58

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New York — Austin

from $57

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New York — Syracuse

from $58

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Top International Destinations from New York

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

New York — London

from $65

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New York — Paris

from $74

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New York — Toronto

from $70

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New York — Rome

from $511

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New York — Montreal

from $74

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New York — Cancun

from $76

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New York — Tokyo

from $71

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New York — Barcelona

from $68

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New York — Aruba

from $71

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New York — Mumbai

from $71

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How to book a plane ticket yourself?

Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
To find a plane ticket, please select dates.