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Flights from Chicago to Gillette

Find the cheapest flight options from Chicago to Gillette over the next three months. Book one-way tickets from SGD 376 and round-trip tickets from SGD 904.

      • ORD 08:20
        6h 17m
        1 stop
        GCC 13:37
        Chicago - Gillette | Sat, Jan 3 | American Airlines
        GCC 14:12
        19h 18m
        1 stop
        ORD 10:30
        Gillette - Chicago | Sun, Jan 4 | United Airlines
        SGD 904 SGD 1,202
        25% OFF
        25% OFF
        SGD 1,202 SGD 904
      • ORD 21:40
        25h 46m
        1 stop
        GCC 22:26
        Chicago - Gillette | Mon, Dec 22 | United Airlines
        GCC 05:26
        27h 18m
        1 stop
        ORD 09:44
        Gillette - Chicago | Fri, Dec 26 | United Airlines
        SGD 952 SGD 1,202
        21% OFF
        21% OFF
        SGD 1,202 SGD 952
      • ORD 07:10
        16h 16m
        1 stop
        GCC 22:26
        Chicago - Gillette | Sat, Jan 3 | United Airlines
        GCC 05:26
        14h 53m
        1 stop
        ORD 21:19
        Gillette - Chicago | Sun, Jan 4 | United Airlines
        SGD 1,070 SGD 1,202
        11% OFF
        11% OFF
        SGD 1,202 SGD 1,070
      • CHI 13:00
        17h 25m
        1 stop
        GCC Invalid Date
        Chicago - Gillette | Fri, Dec 12 | Normal Airline
        GCC 15:00
        6h
        Direct
        CHI 16:00
        Gillette - Chicago | Sun, Dec 14 | Normal Airline
        Find More Flights
        Find More Flights

Displayed flight fares from Chicago to Gillette are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Flight details for Chicago to Gillette

The distance between Chicago and Gillette is 1,475.89 km. Based on Trip.com's data, travel demand peaks in July. The off-season for travel is November.

Cheapest one-way flight priceSGD 376
Cheapest round-trip ticket priceSGD 904
Off-season for travelNovember
Peak season for travelJuly
Flight distance1,475.89 km

Find the best time to fly from Chicago to Gillette

The cheapest time for Chicago to Gillette flights: Dec 14 to Dec 21 — one way flight prices from SGD 375.

Cheapest flights
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  • 714
  • 1421
  • 2128

  • Jan

    284
  • 411
  • 1118
  • 1825

  • Feb

    251
  • 18
  • 815
  • 1522

  • Mar

    221
Displayed fare trends are based on Trip.com's aggregated average of the lowest flight prices from Chicago to Gillette, calculated over the upcoming 10 weeks.

Flight FAQs

  • What are the cheapest flights from Chicago to Gillette (CHI-GCC)?

    Based on Trip.com data, Frontier Airlines offers one-way fares as low as SGD 376 on Cheapest nonstop routes (e.g. MDW to GCC on Mon, Dec 15), while American Airlines offers Cheapest nonstop round-trips from SGD 904 departing on Sat, Jan 3 and returning on Sun, Jan 4.
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to Gillette 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.
  • To find best deals on flights from Chicago to Gillette, 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 Mon, Dec 15, with one-way flights priced at just SGD 376.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Frontier Airlines.
    · 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 Gillette travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Chicago to Gillette is November, when demand for travel is lower.
  • After crunching the numbers on our December flight calendar, it's currently cheapest to fly from Chicago to Gillette on December 22, 2025 with United Airlines, with prices starting at SGD 951.
  • The time difference between Gillette and Chicago is 1h.
  • Tickets can only be changed or canceled 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.