$81 Cheap flight deals from Chicago (CHI) to Bermuda (RIC)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Chicago to Bermuda

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Feb 15 - Thu, Feb 19
ORD
O'Hare Intl.
RIC
Richmond Intl.
$478 Roundtrip, found 2 days ago
$478
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, Feb 15 from O'Hare Intl. to Richmond Intl., returning Thu, Feb 19, priced at $478 found 2 days ago
Sun, Feb 15 - Tue, Feb 17
MDW
Midway Intl.
RIC
Richmond Intl.
$723 Roundtrip, found 2 days ago
$723
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sun, Feb 15 from Midway Intl. to Richmond Intl., returning Tue, Feb 17, priced at $723 found 2 days ago

Airfares from $81 One Way, $160 Round Trip from Chicago to Bermuda

Prices starting at $160 for return flights and $81 for one-way flights to Bermuda were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Apr 16 - Thu, Apr 23
MDW
Chicago
RIC
Richmond
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Chicago to Richmond, returning Thu, Apr 23, priced at $160 found 1 day ago
Mon, Apr 13 - Thu, Apr 16
MDW
Chicago
RIC
Richmond
$170 Roundtrip, found 6 days ago
$170
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Apr 13 from Chicago to Richmond, returning Thu, Apr 16, priced at $170 found 6 days ago
Tue, Mar 17 - Thu, Mar 19
ORD
Chicago
RIC
Richmond
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Mar 17 from Chicago to Richmond, returning Thu, Mar 19, priced at $180 found 1 day ago
Thu, Apr 30 - Sat, May 2
ORD
Chicago
RIC
Richmond
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Chicago to Richmond, returning Sat, May 2, priced at $180 found 1 day ago
Thu, Apr 30 - Sun, May 3
ORD
Chicago
RIC
Richmond
$181 Roundtrip, found 1 hour ago
$181
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Chicago to Richmond, returning Sun, May 3, priced at $181 found 1 hour ago

Bermuda economy flight packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn & Suites Ashland near Kings Dominion
2.5-star property

Quality Inn & Suites Ashland near Kings Dominion

7.2/10 Good! (1,000 reviews)

Apr 2 - Apr 5

3 night stay

Chicago (CHI) to Richmond (RIC)

Southwest Airlines • Coach

Richmond (RIC) to Chicago (CHI)

Frontier Airlines • Coach
Price was $465, price is now $419 per person
$419
per person
found 1 day ago
Unfortunately there were more cons than pros. It sits right beside 95 so lots of car nose, water pressure is bad, carpet and area didn’t look vacuumed or dusted, room smelled moldy, elevator not working and we were on the 2nd floor. I won’t be staying at this hotel again. The only convience was it was near Kings Dominion, breakfast was decent and breakfast area was clean.

Reviewed on Aug 11, 2025

Country Inn & Suites by Radisson, Williamsburg East (Busch Gardens), VA
3.0-star property

Country Inn & Suites by Radisson, Williamsburg East (Busch Gardens), VA

7.4/10 Good! (1,391 reviews)

Apr 3 - Apr 7

4 night stay

Chicago (MDW) to Richmond (RIC)

Southwest Airlines • Roundtrip • Coach
Price was $580, price is now $507 per person
$507
per person
found 21 hours ago
Everything was good and clean

Reviewed on Nov 2, 2025

Quality Inn North
2.5-star property

Quality Inn North

5.6/10 (1,002 reviews)

Apr 2 - Apr 5

3 night stay

Chicago (CHI) to Richmond (RIC)

Southwest Airlines • Coach

Richmond (RIC) to Chicago (CHI)

Frontier Airlines • Coach
Price was $487, price is now $440 per person
$440
per person
found 20 hours ago
The location to Downtown Richmond was great, very quite although right next to highway. Appeared to be a bit old but was clean and comfortable. Breakfast was voucher-ed at the attached diner..which was good. The only odd thing was all the sliding doors to patio's and balconies were now windows that did not open...not sure why but it was still fine and I would stay there again.

Reviewed on Jan 23, 2020

Don't see what you're looking for?
See all available trips from Chicago to Bermuda
View all trips

More About Flying To Bermuda from Chicago

Route Information for Flights from Chicago to Bermuda

Origin Airport IATA Code
CHI
Destination Airport IATA Code
RIC
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Bermuda

Whether you want to book cheap flights from Chicago to Bermuda or are looking for the perfect package holiday, Orbitz is your one-stop source. Taking the stress and expense out of travel, Orbitz helps you find the best fares for Chicago to Bermuda flights.

Make the Most of Your Vacation

Not only does Orbitz have cheap deals for Chicago to Bermuda flights, we can also help you plan your vacation in advance. Why wait in lengthy lines for tickets to shows, amusement parks, and other attractions when you could be making the most of your holiday? Add activities to your flight booking for fewer hassles once you arrive in Bermuda.

Planning on the Go

Book your flights from Chicago to Bermuda wherever you are with the Orbitz app for Android and iPhone. Or simply use m.orbitz.com on your mobile browser to search and book the Chicago to Bermuda flights that you want. And if you’re running late, you check your flight status and baggage claim information on your mobile device too too.

Craft Your Perfect Vacation

Orbitz takes the stress out of vacation planning with great deals on flights from Chicago to Bermuda, hotels, car rentals, cruises, and more. Mix and match results for your perfect trip, or book a complete vacation package.

Keep Informed With Orbitz

With Orbitz’s free alerts service, you will stay informed of flight or services disruptions to your Chicago to Bermuda flights. The alerts can be sent straight to your mobile phone or email.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.