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$306+ Cheap flights from Bermuda to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
BDA — CHI
mar. 6 — mar. 131
vie. 3/6
vie. 3/13
1 adult, Economy
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Cheap flight deals from Bermuda to Chicago

Cheapest flights from Bermuda to Chicago
Explore the most affordable flight options available from Bermuda to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 4, 2026.

This Gotogate deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/208:55 pm
BDA
-
ORD
2 stops25h 15m
Air Canada
vie. 2/278:00 am
ORD
-
BDA
1 stop9h 50m
Air Canada
Deal found 2/2$389
This Trip.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/198:00 am
BDA
-
ORD
1 stop18h 22m
Multiple Airlines
jue. 3/261:55 pm
ORD
-
BDA
1 stop27h 55m
Multiple Airlines
Deal found 2/2$426
This Mytrip deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/178:00 am
BDA
-
ORD
2 stops27h 39m
Multiple Airlines
jue. 2/193:35 pm
ORD
-
BDA
2 stops26h 15m
Multiple Airlines
Deal found 2/1$513
This Expedia deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/208:55 pm
BDA
-
ORD
2 stops25h 15m
Multiple Airlines
vie. 2/276:04 am
ORD
-
BDA
2 stops29h 29m
Multiple Airlines
Deal found 2/2$523
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/198:00 am
BDA
-
ORD
1 stop18h 22m
Multiple Airlines
mar. 3/247:31 pm
ORD
-
BDA
1 stop16h 44m
Multiple Airlines
Deal found 2/2$531
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/198:00 am
BDA
-
MDW
1 stop7h 02m
Multiple Airlines
mar. 3/2411:19 am
MDW
-
BDA
2 stops24h 56m
Multiple Airlines
Deal found 2/2$587
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/201:25 pm
BDA
-
MDW
2 stops22h 56m
Delta
vie. 2/276:20 pm
MDW
-
BDA
2 stops39h 50m
Delta
Deal found 2/2$890
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/178:15 am
BDA
-
MDW
1 stop27h 55m
Multiple Airlines
jue. 2/1911:05 am
MDW
-
BDA
1 stop25h 50m
Multiple Airlines
Deal found 2/1$907
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/213:56 pm
BDA
-
MDW
1 stop8h 35m
Delta
sáb. 3/286:00 am
MDW
-
BDA
1 stop6h 46m
Delta
Deal found 2/4$1,537

Find flight deals from Bermuda to Chicago

Keep the following information in mind while searching for Bermuda to Chicago flight deals. Data was last updated febrero 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$389
(Gotogate)

One-way from

$306
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$657
Provider with most accurate pricing for Hamilton L.F Wade Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hamilton L.F Wade Intl-Chicago (CHI) flights.
Search Deals
From Bermuda to Chicago (CHI)
Search Deals
One-way flight from Bermuda to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 30% potential increase in price ($375 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($60 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Bermuda to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated febrero 4, 2026.
Use the filters below to find and compare flights from Bermuda to Chicago that are best for you.

Fly from

Bermuda

Fly to

Chicago

Route

Depart

Return

Price

HamiltonChicago

BDA - ORD

BDAORD

Hamilton L.F Wade Intl

vie. 2/20

8:55 pm-8:10 pm

2 stops25h 15m

Chicago O'Hare Intl

vie. 2/27

8:00 am-7:50 pm

1 stop9h 50m

$389

HamiltonChicago

BDA - ORD

BDAORD

Hamilton L.F Wade Intl

jue. 3/19

8:00 am-12:22 am

1 stop18h 22m

Chicago O'Hare Intl

jue. 3/26

1:55 pm-7:50 pm

1 stop27h 55m

$426

HamiltonChicago

BDA - ORD

BDAORD

Hamilton L.F Wade Intl

mar. 2/17

8:00 am-9:39 am

2 stops27h 39m

Chicago O'Hare Intl

jue. 2/19

3:35 pm-7:50 pm

2 stops26h 15m

$513

HamiltonChicago

BDA - ORD

BDAORD

Hamilton L.F Wade Intl

vie. 2/20

8:55 pm-8:10 pm

2 stops25h 15m

Chicago O'Hare Intl

vie. 2/27

6:04 am-1:33 pm

2 stops29h 29m

$523

HamiltonChicago

BDA - ORD

BDAORD

Hamilton L.F Wade Intl

jue. 3/19

8:00 am-12:22 am

1 stop18h 22m

Chicago O'Hare Intl

mar. 3/24

7:31 pm-2:15 pm

1 stop16h 44m

$531

HamiltonChicago

BDA - MDW

BDAMDW

Hamilton L.F Wade Intl

jue. 3/19

8:00 am-1:02 pm

1 stop7h 02m

Chicago Midway

mar. 3/24

11:19 am-2:15 pm

2 stops24h 56m

$587

HamiltonChicago

BDA - ORD

BDAORD

Hamilton L.F Wade Intl

sáb. 3/21

8:30 am-7:51 pm

2 stops13h 21m

Chicago O'Hare Intl

sáb. 3/28

7:31 pm-6:00 pm

2 stops20h 29m

$616

HamiltonChicago

BDA - ORD

BDAORD

Hamilton L.F Wade Intl

mar. 2/17

12:05 pm-6:00 pm

1 stop7h 55m

Chicago O'Hare Intl

jue. 2/19

9:55 am-9:50 pm

1 stop9h 55m

$618

HamiltonChicago

BDA - MDW

BDAMDW

Hamilton L.F Wade Intl

vie. 2/20

1:25 pm-10:21 am

2 stops22h 56m

Chicago Midway

vie. 2/27

6:40 pm-2:25 pm

1 stop17h 45m

$890

HamiltonChicago

BDA - MDW

BDAMDW

Hamilton L.F Wade Intl

mar. 2/17

8:15 am-10:10 am

1 stop27h 55m

Chicago Midway

jue. 2/19

11:05 am-2:55 pm

1 stop25h 50m

$907

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 19 results
1
2

Best time to book a flight from Bermuda to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Bermuda with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Bermuda to Chicago
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated febrero 4, 2026.
Peruse reviews from past customers who have flown with American Airlines from Bermuda to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,216 reviews

Entertainment

6.9

Food

6.4

Crew

8.0

Overall

7.2

Comfort

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,216 reviews
American Airlines
7.2
Good
11,216 reviews

Entertainment

6.9

Food

6.4

Crew

8.0

Overall

7.2

Comfort

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Bermuda to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Bermuda to Chicago?

    Air Canada and Delta can get you from Bermuda to Chicago in just under 22h 56m. Your travel time can differ by up to 2h 19m. Bermuda and Chicago are separated by a distance of 1421 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Bermuda to Chicago that include hotel bookings?

    Yes. In addition to deals on Bermuda to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Bermuda to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Bermuda to Chicago.

  • Can I find deals for business class flights from Bermuda to Chicago?

    Yes. Cheapflights offers flight deals from Bermuda to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Bermuda to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Bermuda to Chicago

Discover the top airline that operate flights from Bermuda to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated febrero 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$648Average$714FlexibilityNo cancel feeOn-time71%

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