Cheap flights from George Town to Chicago

Owen Roberts
GCM
Chicago FSS
CHI

Flight deals from George Town to Chicago

Below you can see the best deals on flights George Town — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 5 September, from $267.

Top 10 cheap flights from George Town to Chicago

DL
DL
F9
$ 272

George Town — Chicago

13:04—12:50
1 Sep 2026
8 h 21 m
2 stops
DL
DL
F9
$ 272

George Town — Chicago

13:04—12:50
1 Sep 2026
8 h 23 m
2 stops
DL
DL
F9
$ 277

George Town — Chicago

13:04—12:50
27 Aug 2026
8 h 18 m
2 stops
DL
DL
F9
$ 277

George Town — Chicago

13:04—12:50
27 Aug 2026
8 h 21 m
2 stops
DL
DL
F9
$ 277

George Town — Chicago

13:04—12:50
27 Aug 2026
8 h 24 m
2 stops
DL
DL
F9
$ 277

George Town — Chicago

13:04—12:50
5 Sep 2026
8 h 21 m
2 stops
DL
DL
F9
$ 278

George Town — Chicago

13:04—12:50
2 Sep 2026
8 h 21 m
2 stops
DL
DL
F9
$ 278

George Town — Chicago

13:04—12:50
2 Sep 2026
8 h 23 m
2 stops
DL
DL
F9
$ 288

George Town — Chicago

13:04—12:50
1 Sep 2026
8 h 13 m
2 stops
DL
DL
F9
$ 288

George Town — Chicago

13:04—12:50
1 Sep 2026
8 h 17 m
2 stops

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the George Town — Chicago flight

Looking for cheap flights from George Town to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your George Town — Chicago ticket online at the best price.

The route has direct flights — around 3 flights per week, flights are operated by United Airlines, American Airlines, a nonstop flight takes about 7 h 16 min, the distance between the cities is around 2,572 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $267Min. price
SeptemberCheapest
NovemberPeak season
YesDirect flights
2,572 kmDistance
7 h 16 minTravel time
2Airlines
3 / wkFlights

Flight schedule from George Town to Chicago

The table shows direct flights from George Town to Chicago on the selected date. The flight takes approximately 7 h 16 min. Regular flights are operated by United Airlines and American Airlines. Departures from Owen Roberts International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 08 Aug 2026

Flight ticket prices by day: George Town — Chicago

Below is a calendar of the lowest flight ticket prices for George Town — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $267 in September, and the most expensive are around $373 in November. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from George Town to Chicago by month. Tickets are usually cheapest in October (around $314) and priciest in December (about $501) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$466highMay$326lowSep$326low
Feb$373mediumJun$419highOct$314low
Mar$442highJul$466highNov$361medium
Apr$349mediumAug$396mediumDec$501high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in September and most expensive in November. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a George Town — Chicago ticket

  • Book ahead: fares for George Town — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Flights George Town — Chicago operate on Saturdays — keep that in mind when picking your travel dates.
  • The cheapest month to fly to Chicago is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the George Town — Chicago route are operated by 2 airlines; United Airlines runs the most flights (around 67% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    1x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight GCM → ORD1x/week
      Duration
      4h 23m
      Days
      MTWTFSS
    66.7%Open →
  • American AirlinesAA
    1x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight GCM → ORD1x/week
    33.3%Open →

Cities and airports on the George Town — Chicago route

Flights George Town — Chicago depart from Owen Roberts International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

George Town

GCM
Cayman Islands
About the cityHow to get thereWeatherAll about the country Cayman Islands
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the George Town — Chicago flight

How long is the flight from George Town to Chicago?

A nonstop George Town — Chicago flight takes about 7 h 16 min — the distance between the cities is around 2,572 km.

How far is it from George Town to Chicago?

The distance from George Town to Chicago is about 2,572 km, which a nonstop flight covers in around 7 h 16 min.

Are there direct flights from George Town to Chicago?

Yes, there are nonstop flights George Town — Chicago — around 3 flights per week.

Which airlines fly from George Town to Chicago?

Airlines operating George Town — Chicago include United Airlines, American Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do George Town — Chicago flights use?

Flights from George Town depart from Owen Roberts International Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from George Town to Chicago?

The price of a George Town — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in November. Tickets typically cost between $267 and $373. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights George Town — Chicago?

Flights George Town — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from George Town to Chicago?

To catch a low fare George Town — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from George Town

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MiamiHoustonAtlantaKingstonNew York CityTorontoPanama CityTampaFort LauderdaleCayman BracCharlotteWashington, D.C.Los AngelesNassauOrlandoPhiladelphiaDetroitLittle CaymanDenverMontego BayDallas

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverLondonNashvilleIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

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