Find cheap flights from Bermuda to Chicago

Find cheap flights from Bermuda to Chicago

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Good to know

Low season

JuneBest time to beat the crowds with an average 6% drop in price.

High season

MarchMost popular time to fly with an average 13% increase in price.

Average price round-trip

$491(avg. price over the last 2 weeks)

Good deal round-trip

$422or less

Good deal one-way

$271or less

Top tips for finding cheap flights to Chicago

  • Looking for cheap airfare to Chicago? 25% of our users found tickets to Chicago for the following prices or less: From Hamilton $271 one-way - $346 round-trip
  • High season is considered to be February, March and April. The cheapest month to fly to Chicago is June.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

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Top 3 airlines serving from Bermuda to Chicago

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,181 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Crew was awesome!"
Cons: "The boarding did not go on time. An announcement about why would have been nice. Still made it on the flight on time."

Pros: "Same crew and great experiments again"
Cons: "Nothing"

Pros: "Kosher snacks! Thank you! Very safe and controlled Covid procedures. Made me feel safe."

Pros: "Felt very clean and so glad they are not selling every seat"

Pros: "It was all good glad the last leg of the trip was pleasant."

Pros: "Airplane accelerated from stand-by directly to runway without preparation stop. Awesome!"

Cons: "Small plane, feels cramped"

Cons: "The unfortunate delay prevented me from attending my grandmother’s wake. Fewer delays would be helpful."

Pros: "Crew was friendly"
Cons: "The boarding process was rough and haphazard"

Pros: "The crew did their best to deal with delay."
Cons: "There was an absolutely awful job done by both Delta and Kayak of informing us if additional delays, new gate assignments, when the plane would be reboarded. Also, people were quite angry that the plane had to be cleaned between the time we got off and the time we reboarded. Just get us home."

Cons: "No sandwiches for sale just snack boxes"

Pros: "Taco"
Cons: "Taco"

Pros: "The fight was very professionally carried out."
Cons: "The gate agent hurried ineffectively to board our slightly delayed flight (around 10 min). She left open the Priority Lane and boarded all pax there, having to step 4 steps to the left to scan every boarding pass."

Pros: "It was ok"
Cons: "Seat the family together"

Cons: "Announcements were too loud in earphones (could damage ear drums) and entertainment was turned off while waiting 30 min for the gate to open."

Cons: "Taxied at ORD for 45 minutes waiting for a gate to vacate."

Cons: "Smooth on time flight"

Pros: "The crew really kept us updated on the many delays."
Cons: "There were SO many delays and they kept changing. At one point we got on and off the plane."

Pros: "Flight left on time"
Cons: "Gate crew had trouble identyfing boarding pass on their computer. Difficulty getting on plane"

Pros: "Amazing crew and clean cabin."

Pros: "I loved the flight attendants and the desk staff everyone was so friendly and made me want to travel delta again."
Cons: "Delta doesn’t offer military spouses free checked bags and I found this out at the airport. It was disheartening, but at least it’s Delta and not the airline that is supposed to represent America."

Pros: "On time/ early arrival!"
Cons: "Most bring on 2 large carry ons slowing down boarding an de- planeing."

Cons: "Plane journey awful. Speaker had a loud buzzing noise all the time so never heard a word bad landing. Rattling plane Very cold."

Pros: "Quick flight"
Cons: "Flight attendant spoke like a robot. Could not understand her."

Pros: "On time"
Cons: "Small aircraft"

Pros: "Staff, service, options"

Cons: "Over an hour delay before boarding due to supposedly bad weather. Because flight was overbooked they were offering $400 gift card to change to standby on another flight. If you didn’t make that flight (evening), you’d be confirmed on a flight the following morning with one stop in Detroit (we booked a nonstop to Chicago). Uh, no thanks. Then to top it off, we’ve landed and been told that it will be at least an hour before we can deplane due to no availability at the gate (it’s 1145 pm right now). All this plus their new policy of not allowing us to select our seats because we bought the cheapest tickets. Really Delta? You go ahead and cater to the rich and I’ll choose to fly with another airline."

Pros: "Crew friendly"
Cons: "Middle seat with no option for me to move"

Pros: "Movie"
Cons: "Break downs again... At least this time they found another plane."

Pros: "Flight attendants were pleasant."

Pros: "Friendly service, comfortable seat, on time, no issues."

Cons: "Everything"

Pros: "The crew was great"
Cons: "The flight was 4 hours delayed"

Pros: "I flew on a basic economy fare (I understand the restrictions) and was seated in Economy Comfort +, so that was appreciated."
Cons: "I could see on the Fly Delta app that I had been placed in seat 10B, but neither the app nor my boarding pass gave me a group to board with, so I assumed that I needed to board with group 3, which necessitated gate-checking my rollerboard bag. Only when I approached the gate to board did I notice on the info screen that I had been "upgraded" to Comfort + and granted boarding with the Sky Priority group. I wish this had been clearer so I could have avoided waiting to board and gate-checking my bag. Minor inconvenience but room for improvement on Delta's part."

Pros: "Friendly staff and comfortable seating"

Pros: "This was not my original transfer flight but everyone was much nicer and helpful than serious and being rude. Love Delta, I did not flight United because I wouldn’t have met my United flight once landing in ATL. The Young African American woman who was at the gate was amazing and so reassuring that I would make my flight to Chicago. Would book Delta, just because of how nice she was to me."

Pros: "Flight was on time. Boarded quickly with no fuss."

Pros: "Flt on time, very nice and friendly gate agent and flight attendant"

Cons: "Delayed"

Pros: "The Delta people were solicitous, efficient and brilliant the whole way through. We had not a bit of trouble. Our first class seats were comfortable, but with the supplied blanket, pillow and poor air conditioning it was a hot flight. The cabin personnel were wonderful as per usual, and my tasty gin and tonic soothed any discontent. I wish I could fly this way all the time!"
Cons: "The private contractor handling wheelchair assistance was terrible. A Delta employee theorized that they do not pay enough to attract and retain personnel. Our pre-arranged chair was not there, multiple calls by our Delta assistant finally got us a ride to the chair holding area, but after about 45 minutes we gave up and shuffled off to the security area on foot. Thank goodness my hubby is mobile enough for that to have been an option. When we abandoned our wait we were still 4th in line for an attendant to push the chair. If Delta has any responsibility in this it would be in the retention and compensation for the private contractor."

Cons: "The delta studio didn't work with Android 8"

Pros: "Accident on way to airport, so I showed up to check bags 45 minutes before flight time. They said they couldn't get the bag to the plane..in 45 minutes? So, they put on the next flight... 6 hours later. Said I could fly without the bag... uh, no thanks. They would not look for alternatives without charging me more. Flight attendants were crabby, otherwise everything was fine. I flew British Airways a few months ago. Night and day. Seriously. Delta does not even approach having good service. There was no comparison to British Air--- Delta is not in the same league."

Pros: "Airline stewards were very friendly and pleasant."
Cons: "We booked with Delta, but were put on Air France. Even though we had our boarding passes in hand we had to wait in long, slow line for baggage tags because they would not print from kiosk. There was minimal Air France staff on duty serving thousands of passengers during busy season (July). While the lines grew larger, the staff was reduced from 4 to 2. Another long, slow line for customs, another long slow line for security=Charles De Gaulle airport was awful. We arrived at the airport 4 hours before our departure time and got to our boarding gate with no time to spare."

Pros: "Service was very nice."
Cons: "The flight was insanely delayed. Three hours. With a major product launch the next day, it was not ideal."

Pros: "What I liked: Sky Priority privilege came with separate luggage check-in queues and early boarding"
Cons: "What I disliked: Seats were too small No beverages or snacks offered No USB or power outlets available Three different groups board before Delta Comfort (e.g. those needing more time, travelers with children, first/business class) Didn't see the value compared to a less expensive main cabin ticket"

Pros: "I was notified about the delay via text before I left for the airport, which was nice. I would not have checked my email."
Cons: "Delayed for over 2 hours. I have never flown Delta before this flight and it wasn't a great representation. The flight attendants were nice but I was in a seat near the engine and it was making really weird noises. I fly almost every two weeks, so I'm used to engine noises but this was one of the loudest/most rickety sounding flights I have ever been on.. and I have flown Spirit a few times. It just didn't feel safe. Landing scared me a little too as I have landed in O'Hare countless times and have never flown so low to the highway upon entry. It felt like we were only a couple hundred feet above the cars."

Pros: "We were on time!!!!"
Cons: "I've had friendlier flight attendants"

Cons: "Unnecessary flight cancellation. I had friends taking the same flight at the same time at the same airport from different airlines and they came through for their customers. I received no consolation it assistance with overnight accommodations."

Pros: "We were delayed due to weather and Delta brought a cart of snacks and drinks over to the gate for us."

Pros: "All good, except poor prep on food"
Cons: "As above"

Pros: "Not much"
Cons: "Seating horrible"

Cons: "gate assignment took too long"

Pros: "It is good"

Cons: "No tv on seat. Those dumb comedy tv show"

Pros: "How spacious it felt and there were film selections"
Cons: "My film kept stopping randomly."

Cons: "The boarding experience is awful. I wish that there was more order to the boarding process such as with Southwest Airlines. There is simply no control over rude passengers who push there way to the front."

Pros: "at least flights were on time. 20 minutes delay is not bad."

Pros: "Nothing."
Cons: "Cramped, claustrophobic space. Cabin too warm."

Pros: "It was very inexpensive and on time. And it was much more comfortable than those budget airlines like Spirit, Frontier, etc."
Cons: "The snack choice was unappealing."

Cons: "The touch-screen entertainment system was not very responsive. It was difficult to get the screen to recognize your selection."

Pros: "Aircraft comfort and entertainment options"

Pros: "I like it! Thank you, kayak"

Pros: "Friendly and prompt service."

Pros: "personal entertainment systems and charging plugs"
Cons: "only pretzels and no headphones offered for the entertainment systems."

Cons: "Aircraft need to be updated. Or price should be credited when you get such an old aircraft."

Pros: "Entertainment and great beverage options"

Pros: "Seat were comfortable and I didn't feel claustrophobic."

Pros: "Todo muy bueno"

Pros: "The staff was friendly and helpful"
Cons: "There was a ton of turbulence"

Cons: "Boarding late"

Pros: "Friendly staff Smooth ride On time"

Cons: "Always delayed"

Pros: "NOTHING"
Cons: "Everything. DELAYS___DELAYS"

Pros: "Pretty comfortable"

Pros: "On time."

Cons: "Got cancelled"

Cons: "I am still not feeling well to travel, so I was staying at home and no Madrid, may be in the fall or winter when I get better, I will visit Madrid one more time."

Pros: "very smooth, ontime ride.. kool"
Cons: "everything was ok"

Pros: "Delays caused a little stress but all in all a good experience."
Cons: "Late arrival to DCA."

Pros: "The TIMING AND ATMOSPHERE"

Pros: "Upon sitting down, I was able to fall asleep almost instantly. The helpful stewardesses were constantly aware of my needs."
Cons: "Check-in desk seemed confused and unorganized. Two very friendly ladies were helping out but were on different wavelengths."

Cons: "Numerous delays and disappointments. Two delays before boarding. Another long delay after boarding waiting for paperwork to be completed. Long taxi period. Waited over half hour for baggage claim conveyor to start rolling."

Pros: "Very professional"
Cons: "We didn't leave on time"

Pros: "Everyone was gracious and very helpful. Wheel chairs waiting at each stop. Special ramp installed at CHO, VERY HELPFUL."

Cons: "EXTREMELY LONG CHECK IN & SECURITY LINES"

Pros: "On time arrival despite two issues at the departure gate"

Pros: "Service, comfort, timeliness."
Cons: "Food was marginal, especially the chicken in the salad, which was petrified."

Pros: "It was fine. I was comfortable and I slept throat most of it."

Pros: "Not much"
Cons: "We sat on the tarmac for an hour after we landed. Missed my connection, no other flights that night. It wasn't even 10 pm yet."

Pros: "Everything was very professional."

Cons: "90 min late"

Pros: "A breakfast offering at any time would be great."
Cons: "Too many people getting on at same time."

Pros: "Boarding was smooth"
Cons: "It was fine"

Pros: "Good"

Pros: "Roomy & comfortable seating for such a small aircraft"
Cons: "Late boarding, over an hour"

Cons: "Gate changed and baoarding time changed countless times."

Cons: "No tv."

Pros: "Both planes were delayed"
Cons: "I did not appreciated getting to my destination so late."

Pros: "This was ok"

Pros: "Can't sleep sitting up. Pretty funny watching everyone try..."

Pros: "Easy process with no delays"

Pros: "All was well"
Cons: "I had no real complaints"

Pros: "you guys have tvs in the headrest and its spacious in the seating area. you all treated me way better than spirit airlines!"

Pros: "All good"

Pros: "Nothing"
Cons: "Turbulence"

Pros: "Great service. Free Internet and movi9"
Cons: "Seat next to the restroom"

Pros: "Cleanliness of plane"

Pros: "Great staff. Great safety explanation. Smooth fight"
Cons: "Nothing. Everything was great. I'll definitely try to stick with united for my future travels"

Pros: "arrived on time despite delayed departure"

Cons: "Left about 15 minutes late. But we didn't miss any connections so everything turned out okay."

Pros: "Polite staff"

Pros: "Flights was ontime"
Cons: "Plane was too hot, and then way to cold. This seems to be a re-occurring problem. I am not sure why the plane can't just be set to be be 68-72 degrees. There is no need for it to be above 80 or less than 60."

Pros: "Price was lowest for that date and itinerary."
Cons: "Feels like United is second class compared to other carriers. I purchased this for my Morher-n-Law who rarely flies was traveling by herself. there were 7 gate changes 3 day of. I Was very concerned if she would make it."

Pros: "Lots of turbulence"

Cons: "Delayed three times"

Pros: "Nice plane for a small one"
Cons: "Bumpy ride."

Cons: "Two time delayed"

Pros: "Polite and pleasant attendants"
Cons: "nothing"

Cons: "My luggage did not make it to my destination."

Pros: "Constant updates by email. Very informative"
Cons: "Nothing"

Pros: "On time, boarded quickly, checked my carry on all the way through Tampa for me"

Pros: "The price"
Cons: "I was unable to board because I didn't see the boarding time. This should be available even if it is just an estimated time. This way if I am running late I know what time I have to be there."

Cons: "Departure from Chicago was delayed"

Cons: "The very very long delay"

Pros: "Everything went smooth"

Pros: "Check-staff was very gracious."

Pros: "No problems"
Cons: "Little bumpy but bad weather"

Pros: "Friendly service, nice and comfortable."

Pros: "Food was good"
Cons: "Dinner was served within 1 hr of takeoff and breakfast 1-2 hrs of landing. Nothing served inbetween. There was about 10-11 hrs of nothing. No drinks or snacks served. Very poor service in compairison to other international flights I have taken."

Pros: "Staff was very nice"
Cons: "Two flights, two delays."

Cons: "I cancelled it and it appears it didn't really cancel"

Pros: ". We got back 30minutes early then schedule!"

Pros: "Pilot got is there 25 min early"

Pros: "Cost Ease of booking"
Cons: "delays (weather based )"

Pros: "On time."

Pros: "Everything else was fine"
Cons: "Not a lot of smiles"

Pros: "Still deciding"
Cons: "All flights were late."

Pros: "Quick check in!"

Cons: "Delayes"

Pros: "Trip was on time and a good experience overall."
Cons: "No Coffee"

Cons: "Lack of comfortable space. :-("

Pros: "I like the complementary soda. The boarding groups system is smart."
Cons: "I don't care for the wifi options. Loud children."

Pros: "Excellent"

Pros: "On time"

Pros: "As pleasant as possible."
Cons: "Nothing negative to note."

Pros: "Attendant was attentive to her job."
Cons: "The aircraft is uncomfortable."

Pros: ".The attendant was caring and efficient."
Cons: "The boarding process seems to be a cluster of misguided sheep. The aircraft is uncomfortable even for us thinner patrons."

Cons: "The plane was just small and I'm a big guy."

Pros: "I was so comfortable and I got to sleep"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Bermuda to Chicago

Airlines flying from Bermuda to Chicago have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Bermuda to Chicago

Mandatory masks

Masks required on board, masks provided on flights from Bermuda to Chicago

Social distancing seating

Middle seats unavailable to book on flights from Bermuda to Chicago

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Bermuda to Chicago

Book cheap flights from Bermuda to Chicago

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