$316 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 3/7. 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

Wed, Mar 25 - Mon, Mar 30
Multiple Airlines Logo
8:30 am - 12:22 am
BDA
-
ORD
17h 52m
1 stop
Multiple Airlines Logo
7:05 pm - 2:15 pm
ORD
-
BDA
41h 10m
2 stops
$531Multiple Airlines
Wed, Mar 25 - Mon, Mar 30
Multiple Airlines Logo
8:30 am - 12:22 am
BDA
-
ORD
17h 52m
1 stop
Multiple Airlines Logo
7:05 pm - 2:15 pm
ORD
-
BDA
41h 10m
2 stops
$554Multiple Airlines
Wed, Mar 25 - Mon, Mar 30
United Airlines Logo
2:45 pm - 8:15 pm
BDA
-
ORD
7h 30m
1 stop
United Airlines Logo
6:00 am - 1:40 pm
ORD
-
BDA
5h 40m
1 stop
$688United Airlines
Wed, Mar 25 - Mon, Mar 30
American Airlines Logo
8:30 am - 7:55 pm
BDA
-
ORD
13h 25m
1 stop
American Airlines Logo
6:44 pm - 3:03 pm
ORD
-
BDA
18h 19m
1 stop
$700American Airlines
Mon, Apr 6 - Mon, Apr 13
American Airlines Logo
3:53 pm - 12:06 am
BDA
-
ORD
10h 13m
1 stop
American Airlines Logo
8:46 pm - 3:03 pm
ORD
-
BDA
16h 17m
1 stop
$713American Airlines
Wed, Mar 25 - Mon, Mar 30
Multiple Airlines Logo
8:30 am - 7:51 pm
BDA
-
ORD
13h 21m
2 stops
Multiple Airlines Logo
5:05 am - 9:25 pm
ORD
-
BDA
14h 20m
2 stops
$714Multiple Airlines
Wed, Mar 25 - Mon, Mar 30
American Airlines Logo
12:05 pm - 6:00 pm
BDA
-
ORD
7h 55m
1 stop
American Airlines Logo
5:00 pm - 3:03 pm
ORD
-
BDA
20h 03m
1 stop
$720American Airlines
Wed, Mar 25 - Mon, Mar 30
Multiple Airlines Logo
8:00 am - 2:16 pm
BDA
-
ORD
32h 16m
3 stops
Multiple Airlines Logo
7:17 am - 9:25 pm
ORD
-
BDA
12h 08m
2 stops
$787Multiple Airlines
Wed, Mar 25 - Mon, Mar 30
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
$818Delta
Wed, Mar 25 - Mon, Mar 30
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
$1,017Delta
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.

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, with an average flight price of $141.

Find deals

Good to know

Low seasonMay
Cheapest flight$316
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

  • 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 13,190 direct flights from within Bermuda to Chicago. The most common day for departures is Monday, with 16% 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.
7.2
American AirlinesOverall score based on 11339 reviews
7.2Comfort
7.5Boarding
8.0Crew
6.9Entertainment
6.4Food
Airline reviews

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.

2.0 MediocreMarius, Feb 2026
LGA - ORD
Read more American Airlines reviews

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.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

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
Munster
Schererville
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.
First Class flights to Chicago
Business Class flights to Chicago
Premium Economy Class flights to Chicago
Economy Class flights to Chicago