$293 Find Cheap Flights from the Cayman Islands to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 7/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from the Cayman Islands to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from the Cayman Islands to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from the Cayman Islands to Chicago

Sat, Jul 26 - Sat, Aug 2
American Airlines Logo
3:05 pm - 11:57 pmGCM-ORD
8h 52m1 stop
American Airlines Logo
6:25 pm - 11:22 amORD-GCM
16h 57m1 stop
$615American Airlines
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Sat, Jul 26 - Sat, Aug 2
American Airlines Logo
12:10 pm - 9:31 pmGCM-ORD
9h 21m2 stops
American Airlines Logo
10:05 pm - 2:29 pmORD-GCM
16h 24m1 stop
$619American Airlines
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Sat, Jul 26 - Sat, Aug 2
United Airlines Logo
1:45 pm - 6:07 pmGCM-ORD
4h 22mnonstop
United Airlines Logo
7:35 pm - 12:30 pmORD-GCM
16h 55m1 stop
$625United Airlines
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Sat, Jul 26 - Sat, Aug 2
Logo
8:50 am - 7:50 amGCM-ORD
23h 00m2 stops
Logo
9:10 pm - 5:20 pmORD-GCM
20h 10m2 stops
$728
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Sat, Jul 26 - Sat, Aug 2
Logo
11:25 am - 9:49 pmGCM-ORD
34h 24m3 stops
Logo
9:10 pm - 5:20 pmORD-GCM
20h 10m2 stops
$749
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Sat, Jul 26 - Sat, Aug 2
Logo
11:25 am - 9:49 pmGCM-ORD
34h 24m3 stops
Logo
6:02 pm - 5:20 pmORD-GCM
23h 18m3 stops
$786
Find Deal
Sat, Jul 26 - Sat, Aug 2
Delta Logo
1:07 pm - 9:42 pmGCM-MDW
8h 35m1 stop
Delta Logo
6:00 am - 11:42 amMDW-GCM
5h 42m1 stop
$1,168Delta
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KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From George Town $599 round-trip.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $119.

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Good to know

Low seasonSeptember
High seasonNovember
Cheapest flight$293
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from George Town to Chicago

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    Out of the 3 airports in Chicago, Chicago Midway Airport is the nearest to the city center (9 miles). You'll travel 16 miles to reach the center of Chicago if you land in Chicago O'Hare Airport and 79 miles if you land in Chicago Greater Rockford.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $470. The cheapest price found on KAYAK in the last 2 weeks cost $301 and departed from George Town Owen Roberts Intl Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Sunday where round-trip tickets can be as cheap as $568. On the other hand, the most expensive day to fly is Wednesday, where round-trip prices are $1,867 on average.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Chicago?

    The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost $615 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is $666.

  • How many direct flights to Chicago are there each week?

    Each week there are around 11,562 direct flights from within Cayman Islands to Chicago. The most common day for departures is Friday, with 15% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $303 or less one-way and $599 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicago
Business Class flights to Chicagofrom $1,011
Prem Econ Class flights to Chicagofrom $920
Economy Class flights to Chicagofrom $495

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