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Cheap Flights from New York to Chicago

Explore the cheapest flights from New York to Chicago in the next three months. Based on Trip.com's data from the latest 7 days, one-way direct flights start at S$ 111, and round-trip direct tickets start at S$ 212.

      • Cheapest nonstop
        LGA 06:00
        2h 41m
        Direct
        ORD 07:41
        New York - Chicago | Wed, Jun 24 | Delta Air Lines
        ORD 20:10
        2h 30m
        Direct
        LGA 23:40
        Chicago - New York | Fri, Jun 26 | Delta Air Lines
        S$ 212 S$ 242
        12% off
        12% off
        S$ 242 S$ 212
      • JFK 19:30
        3h
        Direct
        ORD 21:30
        New York - Chicago | Wed, Jun 24 | Jetblue Airways
        ORD 19:00
        2h 29m
        Direct
        LGA 22:29
        Chicago - New York | Fri, Jun 26 | Delta Air Lines
        S$ 215 S$ 242
        11% off
        11% off
        S$ 242 S$ 215
      • JFK 15:00
        3h 6m
        Direct
        ORD 17:06
        New York - Chicago | Tue, Jul 7 | Delta Air Lines
        ORD 18:00
        2h 37m
        Direct
        JFK 21:37
        Chicago - New York | Fri, Jul 10 | Delta Air Lines
        S$ 216 S$ 242
        11% off
        11% off
        S$ 242 S$ 216
      • LGA 06:25
        2h 45m
        Direct
        ORD 08:10
        New York - Chicago | Wed, Jun 24 | American Airlines
        ORD 20:10
        2h 30m
        Direct
        LGA 23:40
        Chicago - New York | Fri, Jun 26 | Delta Air Lines
        S$ 218
        10% off
        S$ 242 S$ 218
      • LGA 06:00
        2h 32m
        Direct
        ORD 07:32
        New York - Chicago | Thu, Jul 9 | Delta Air Lines
        ORD 09:30
        2h 16m
        Direct
        LGA 12:46
        Chicago - New York | Mon, Jul 13 | Delta Air Lines
        S$ 220
        9% off
        S$ 242 S$ 220
      • JFK 07:20
        2h 53m
        Direct
        ORD 09:13
        New York - Chicago | Thu, Jul 16 | Delta Air Lines
        ORD 17:35
        2h 25m
        Direct
        LGA 21:00
        Chicago - New York | Mon, Jul 20 | Delta Air Lines
        S$ 220
        9% off
        S$ 242 S$ 220
      • JFK 07:30
        2h 55m
        Direct
        ORD 09:25
        New York - Chicago | Tue, Jun 23 | Delta Air Lines
        ORD 13:46
        5h 58m
        1 stop
        EWR 20:44
        Chicago - New York | Fri, Jun 26 | Delta Air Lines
        S$ 214
        12% off
        S$ 242 S$ 214
      • EWR 13:00
        4h 26m
        1 stop
        ORD 16:26
        New York - Chicago | Thu, Jun 11 | Delta Air Lines
        ORD 06:00
        2h 12m
        Direct
        LGA 09:12
        Chicago - New York | Wed, Jun 17 | Delta Air Lines
        S$ 216
        11% off
        S$ 242 S$ 216
      • EWR 13:00
        6h 29m
        1 stop
        ORD 18:29
        New York - Chicago | Mon, Jun 22 | Delta Air Lines
        ORD 06:00
        2h 12m
        Direct
        LGA 09:12
        Chicago - New York | Thu, Jun 25 | Delta Air Lines
        S$ 216
        11% off
        S$ 242 S$ 216
      • EWR 06:00
        5h 50m
        1 stop
        ORD 10:50
        New York - Chicago | Tue, Jun 16 | Delta Air Lines
        ORD 20:10
        2h 30m
        Direct
        LGA 23:40
        Chicago - New York | Tue, Jun 23 | Delta Air Lines
        S$ 219
        10% off
        S$ 242 S$ 219
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Wed, May 20 | Normal Airline
        CHI 15:00
        6h
        Direct
        NYC 16:00
        Chicago - New York | Fri, May 22 | Normal Airline
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      • Cheapest nonstop
        JFK 07:30
        2h 55m
        Direct
        ORD 09:25
        New York - Chicago | Wed, Jul 1 | Delta Air Lines
        S$ 111 S$ 125
        11% off
        11% off
        S$ 125 S$ 111
      • LGA 06:00
        2h 41m
        Direct
        ORD 07:41
        New York - Chicago | Fri, Jun 12 | Delta Air Lines
        S$ 112 S$ 125
        10% off
        10% off
        S$ 125 S$ 112
      • LGA 07:30
        2h 44m
        Direct
        ORD 09:14
        New York - Chicago | Tue, Jul 7 | Delta Air Lines
        S$ 112 S$ 125
        10% off
        10% off
        S$ 125 S$ 112
      • JFK 07:30
        2h 55m
        Direct
        ORD 09:25
        New York - Chicago | Thu, Jun 18 | Delta Air Lines
        S$ 112
        10% off
        S$ 125 S$ 112
      • LGA 18:50
        2h 55m
        Direct
        ORD 20:45
        New York - Chicago | Thu, Jun 25 | Delta Air Lines
        S$ 112
        10% off
        S$ 125 S$ 112
      • JFK 07:30
        2h 55m
        Direct
        ORD 09:25
        New York - Chicago | Wed, Jun 24 | Delta Air Lines
        S$ 112
        10% off
        S$ 125 S$ 112
      • LGA 06:00
        2h 47m
        Direct
        ORD 07:47
        New York - Chicago | Fri, May 29 | Delta Air Lines
        S$ 112
        10% off
        S$ 125 S$ 112
      • LGA 14:50
        3h
        Direct
        ORD 16:50
        New York - Chicago | Sun, Jun 21 | Delta Air Lines
        S$ 113
        10% off
        S$ 125 S$ 113
      • LGA 20:45
        2h 51m
        Direct
        ORD 22:36
        New York - Chicago | Wed, Jul 15 | Delta Air Lines
        S$ 113
        10% off
        S$ 125 S$ 113
      • EWR 07:05
        8h 20m
        1 stop
        ORD 14:25
        New York - Chicago | Sun, Jul 12 | Delta Air Lines
        S$ 112
        10% off
        S$ 125 S$ 112
      • NYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        New York - Chicago | Wed, May 20 | Normal Airline
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Trip.com Price Insights on Flights from New York to Chicago.

What is the cheapest month for one-way flights from to Chicago?

The average price of one-way flights from to Chicago purchased by Trip.com users by month over the past 12 months.

Based on Trip.com’s data, the cheapest month for flights from to Chicago is November, with an average price of S$ 113, and the most expensive month is July, with an average price of up to S$ 273.

S$ 273
S$ 193
S$ 113
S$ 33
    Cheapest
  • S$ 211
    May
  • S$ 256
    Jun
  • S$ 273
    Jul
  • S$ 238
    Aug
  • S$ 226
    Sep
  • S$ 169
    Oct
  • S$ 113
    Nov
  • S$ 181
    Dec
  • S$ 136
    Jan
  • S$ 146
    Feb
  • S$ 119
    Mar
  • S$ 189
    Apr

What is the cheapest month for round-trip flights from to Chicago?

The average price of round-trip flights from to Chicago purchased by Trip.com users by month over the past 12 months.

Based on Trip.com’s data, the cheapest month for round-trip flights from to Chicago is January, with an average price of S$ 215, and the most expensive month is July, with an average price of up to S$ 529.

S$ 529
S$ 372
S$ 215
S$ 58
    Cheapest
  • S$ 317
    May
  • S$ 337
    Jun
  • S$ 529
    Jul
  • S$ 471
    Aug
  • S$ 333
    Sep
  • S$ 375
    Oct
  • S$ 360
    Nov
  • S$ 322
    Dec
  • S$ 215
    Jan
  • S$ 327
    Feb
  • S$ 332
    Mar
  • S$ 332
    Apr

What is the cheapest day to fly from New York to Chicago during Hari Raya Haji?

Based on Trip.com's data over the past 3 days, these are the lowest one-way airfares from New York to Chicago during Hari Raya Haji.

Hari Raya Haji is scheduled on May 27. The flights from New York to Chicago are cheapest on May 27, with the lowest fare of S$ 116.

S$ 221
S$ 169
S$ 116
S$ 64
    Cheapest
  • S$ 126
    23
    May
  • S$ 128
    24
  • S$ 221
    25
  • S$ 126
    26
  • S$ 116
    27
  • S$ 120
    28
  • S$ 132
    29

Frequently Asked Questions

  • Which airlines offer the cheapest flights from New York (NYC) to Chicago (CHI)?

    Based on Trip.com data, Delta Air Lines offers one-way fares as low as S$ 111 on Cheapest nonstop routes (e.g. JFK to ORD on Wed, Jul 1), while Delta Air Lines offers Cheapest nonstop round-trips from S$ 212 departing on Wed, Jun 24 and returning on Fri, Jun 26.
  • At the moment, you can catch a direct flight from New York to Chicago with the following airlines, including: Delta Air Lines American Airlines Jetblue Airways United Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.
  • It takes about 3 hours 54 minutes to fly from New York (NYC) to Chicago (CHI).
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from New York to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • Based on Trip.com data in the past 4 weeks, there is 42 flight per week flying from New York to Chicago. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA1777 (08:48) United Airlines: S/M/T/-/-/-/- -- UA1210 (12:45)
  • To find best deals on flights from New York to Chicago, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Wed, Jul 1, with one-way flights priced at just S$ 111.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Delta Air Lines.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from New York to Chicago is October, when demand for travel is lower.
  • After crunching the numbers on our May flight calendar, it's currently cheapest to fly from New York to Chicago on May 21, 2026 with Spirit Airlines, with prices starting at S$ 134.
  • You can land at any one of the following hubs in Chicago, with John F. Kennedy International Airport to Chicago O'Hare International Airport (JFK-ORD) is by far the most common option on this route: Chicago O'Hare International Airport (ORD) Chicago Midway International Airport (MDW) Chicago Rockford International Airport (RFD).
  • The time difference between Chicago and New York is 1h.
  • Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

Find Cheap Flights & Deals on Trip.com

Note: Prices shown on this page are the lowest estimated prices found in the last 24 hours and include all taxes and fees.

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Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are shown before payment. Charges for checked baggage, meals, Wi-Fi, and other optional services may also appear in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours, and with many routes refreshed in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.