$227 Find Cheap Flights from the Cayman Islands to Chicago - Compare and Save

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 10/31. 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, 0 bags

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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

Mon, Sep 14 - Thu, Sep 17
Multiple Airlines Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
Multiple Airlines Logo
2:15 pm - 8:55 pm
ORD
-
GCM
30h 40m
2 stops
$434Multiple Airlines
Thu, Sep 10 - Thu, Sep 17
Multiple Airlines Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
Multiple Airlines Logo
2:15 pm - 8:55 pm
ORD
-
GCM
30h 40m
2 stops
$454Multiple Airlines
Thu, Sep 10 - Thu, Sep 17
Multiple Airlines Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
Multiple Airlines Logo
8:40 pm - 8:55 pm
ORD
-
GCM
24h 15m
2 stops
$477Multiple Airlines
Mon, Aug 17 - Sat, Sep 19
Air Canada Logo
12:25 pm - 4:42 pm
GCM
-
ORD
28h 17m
1 stop
Air Canada Logo
3:40 pm - 11:25 am
ORD
-
GCM
43h 45m
2 stops
$499Air Canada
Mon, Sep 14 - Thu, Sep 17
Multiple Airlines Logo
7:00 am - 9:00 am
GCM
-
ORD
26h 00m
2 stops
Multiple Airlines Logo
2:15 pm - 8:55 pm
ORD
-
GCM
30h 40m
2 stops
$499Multiple Airlines
Fri, Oct 9 - Sun, Oct 11
Multiple Airlines Logo
7:00 am - 2:55 pm
GCM
-
ORD
31h 55m
2 stops
Multiple Airlines Logo
8:40 pm - 11:30 am
ORD
-
GCM
14h 50m
1 stop
$583Multiple Airlines
Mon, Aug 17 - Sat, Sep 19
Air Canada Logo
12:25 pm - 7:51 am
GCM
-
ORD
19h 26m
2 stops
Air Canada Logo
6:21 pm - 11:25 am
ORD
-
GCM
41h 04m
2 stops
$629Air Canada
Thu, Sep 10 - Thu, Sep 17
Multiple Airlines Logo
12:25 pm - 11:40 pm
GCM
-
ORD
11h 15m
2 stops
Multiple Airlines Logo
2:15 pm - 8:55 pm
ORD
-
GCM
30h 40m
2 stops
$630Multiple Airlines
Fri, Oct 9 - Sun, Oct 11
American Airlines Logo
8:00 am - 11:33 pm
GCM
-
ORD
15h 33m
1 stop
American Airlines Logo
5:18 am - 11:30 am
ORD
-
GCM
6h 12m
1 stop
$681American Airlines
Thu, Sep 10 - Thu, Sep 17
American Airlines Logo
12:36 pm - 10:31 pm
GCM
-
ORD
9h 55m
1 stop
American Airlines Logo
7:00 pm - 11:10 am
ORD
-
GCM
16h 10m
1 stop
$681American Airlines
Booking Insights

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 the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Saturday where round-trip tickets can be as cheap as $479. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $2,559 on average.

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

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost $571 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $707.

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 $529 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 $176.

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Good to know

Cheapest flight

$227
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 $529. The cheapest price found on KAYAK in the last 2 weeks cost $218 and departed from George Town Owen Roberts Intl Airport.

  • 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.

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

    Each week there are around 30,501 direct flights from within Cayman Islands to Chicago. The most common day for departures is Sunday, 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 $333 or less one-way and $529 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Munster
Schererville
Chesterton
Porter
Monticello
Saint John
Griffith

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 Chicago
Premium Economy Class flights to Chicagofrom $1,722
Economy Class flights to Chicagofrom $329