$301 Find Cheap Flights from Bermuda 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 4/22. 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

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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Flight Deals

Cheap Flights from Bermuda to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Bermuda 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 Bermuda to Chicago

Fri, Jun 19 - Sun, Jul 5
Air Canada Logo
1:45 pm - 2:55 pm
BDA
-
ORD
27h 10m
1 stop
Air Canada Logo
5:35 pm - 12:20 pm
ORD
-
BDA
16h 45m
1 stop
$550Air Canada
Fri, Jun 19 - Sun, Jul 5
Air Canada Logo
1:45 pm - 1:22 pm
BDA
-
ORD
25h 37m
1 stop
Air Canada Logo
8:45 am - 12:20 pm
ORD
-
BDA
25h 35m
2 stops
$554Air Canada
Fri, Jun 12 - Mon, Jun 15
Air Canada Logo
1:45 pm - 7:25 pm
BDA
-
ORD
7h 40m
1 stop
Air Canada Logo
6:22 pm - 12:45 pm
ORD
-
BDA
40h 23m
2 stops
$560Air Canada
Fri, Aug 14 - Fri, Aug 21
Air Canada Logo
1:20 pm - 1:22 pm
BDA
-
ORD
26h 02m
1 stop
Air Canada Logo
9:50 am - 12:20 pm
ORD
-
BDA
24h 30m
1 stop
$607Air Canada
Thu, Apr 23 - Thu, Apr 30
Multiple Airlines Logo
8:00 am - 11:42 am
BDA
-
ORD
29h 42m
1 stop
Multiple Airlines Logo
4:28 pm - 1:50 pm
ORD
-
BDA
19h 22m
2 stops
$612Multiple Airlines
Sun, Mar 29 - Fri, Apr 3
Air Canada Logo
6:50 pm - 6:53 pm
BDA
-
ORD
26h 03m
2 stops
Air Canada Logo
9:50 am - 7:50 pm
ORD
-
BDA
8h 00m
1 stop
$645Air Canada
Sun, Apr 5 - Sun, Apr 12
Multiple Airlines Logo
8:00 am - 12:22 am
BDA
-
ORD
18h 22m
1 stop
Multiple Airlines Logo
5:05 am - 9:25 pm
ORD
-
BDA
38h 20m
2 stops
$650Multiple Airlines
Mon, Mar 30 - Sat, Apr 4
Delta Logo
3:56 pm - 8:53 am
BDA
-
MDW
18h 57m
2 stops
Delta Logo
1:10 pm - 12:13 pm
MDW
-
BDA
21h 03m
2 stops
$907Delta
Sat, Mar 28 - Sat, Apr 4
Delta Logo
3:56 pm - 10:31 pm
BDA
-
MDW
8h 35m
1 stop
Delta Logo
1:10 pm - 12:13 pm
MDW
-
BDA
21h 03m
2 stops
$924Delta
Mon, Mar 30 - Sat, Apr 4
Delta Logo
3:56 pm - 10:31 pm
BDA
-
MDW
8h 35m
1 stop
Delta Logo
6:00 am - 2:46 pm
MDW
-
BDA
6h 46m
1 stop
$1,113Delta
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 flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Hamilton, at $550 return. The most popular connection is from Boston to Chicago and KAYAK users have found round-trip deals for as low as $130 in the last 3 days.

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 $161.

Good to know

Low seasonJune
Cheapest flight$301
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 23% lower on average.
Flight from Hamilton to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Hamilton, at $550 return. The most popular connection is from Boston to Chicago and KAYAK users have found round-trip deals for as low as $130 in the last 3 days.

  • Which Chicago airport is closest to central Chicago?

    9 miles away from Chicago’s city center, Chicago Midway Airport is the closest of the 3 major airports in the city. There are 16 miles separating Chicago city center to Chicago O'Hare Airport, and 79 miles to Chicago Greater Rockford.

  • 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 15,559 direct flights from within Bermuda to Chicago. The most common day for departures is Tuesday, with 15% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airline flying from Bermuda to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Bermuda to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11403 reviews
6.4Food
7.5Boarding
6.9Entertainment
7.2Comfort
8.0Crew
Airline reviews

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

6.0 GoodIrene, Mar 2026
SFO - ORD
Read more American Airlines reviews

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Flight from CHI to PVD was delayed by over 20 hours.

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
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

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.