Find flights
Insights
When to book
FAQs & Tips
Direct Flights
Airlines
Deals

Find cheap flights from Bermuda to Chicago from $300

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 5/27. 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
0 bags
jue. 5/23
jue. 5/30

Search 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
In the last 7 days travelers have searched 44,632,927 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Flights to Chicago - Travel Insights & Trends

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 day to fly to Chicago?

The average price of all flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where tickets can be as cheap as $534. On the other hand, the most expensive day to fly is Tuesday, where prices are $729 on average.

What is the cheapest time of day to fly to Chicago?

The average price for all flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago is generally in the afternoon, when flights cost $604 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is $706.

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 Midway Airport, with an average flight price of $121.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 86% of all flights arriving there.

How long is the flight to Chicago?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from Hamilton, which takes 6h 37m.

How many direct flights to Chicago are there each day?

There are around 1,692 direct flights from within Bermuda to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 51% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 11,842 direct flights from within Bermuda to Chicago. The most common day for departures is Thursday, with 16% of flights taking off on this day.

Good to know

Low season

April

High season

May

Cheapest flight

$300
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 22% 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.

  • Which airline offers the most flights to Chicago?

    Of the 14 airlines that fly to Chicago, United Airlines offers the most flights, with around 5,064 per week, followed by American Airlines with 3,803 flights per week.

See more FAQs

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.

Prefer to fly non-stop to Chicago?

Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Nonstop departures

Bermuda to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Nonstop returns

Chicago to Bermuda

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

See more direct flights
See more direct flights

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.
7.3
American AirlinesOverall score based on 14914 reviews
7.6boarding
7.1entertainment
6.6food
8.0crew
7.2comfort
Airline reviews

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

10.0 ExcellentWilliam, Apr 2024FWA - ORD
Read more about American Airlines reviews

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Book cheap flights from Bermuda to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
5/10vie.
1 stopAmerican Airlines
8h 33mBDA-ORD
5/12dom.
1 stopAmerican Airlines
7h 55mORD-BDA
$380
5/3vie.
1 stopDelta
6h 37mBDA-ORD
5/7mar.
1 stopDelta
16h 00mORD-BDA
$381
6/4mar.
1 stopAmerican Airlines
8h 33mBDA-ORD
6/11mar.
2 stopsAmerican Airlines
7h 41mORD-BDA
$384
5/10vie.
1 stopDelta
9h 01mBDA-ORD
5/12dom.
2 stopsDelta
23h 13mORD-BDA
$442
5/18sáb.
1 stopUnited Airlines
7h 38mBDA-ORD
5/22mié.
1 stopUnited Airlines
5h 35mORD-BDA
$472
5/10vie.
3 stops
23h 35mBDA-ORD
5/12dom.
1 stop
13h 58mORD-BDA
$482
5/10vie.
3 stops
23h 35mBDA-ORD
5/12dom.
2 stops
12h 10mORD-BDA
$537
6/4mar.
2 stopsAmerican Airlines
9h 43mBDA-ORD
6/11mar.
2 stopsAmerican Airlines
7h 41mORD-BDA
$547
5/18sáb.
2 stopsAmerican Airlines
9h 22mBDA-ORD
5/22mié.
1 stopAmerican Airlines
6h 40mORD-BDA
$572
6/21vie.
1 stopAmerican Airlines
27h 25mBDA-ORD
6/24lun.
1 stopAmerican Airlines
28h 42mORD-BDA
$663

Search by stops

Search by airline

Search by price

Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
5/27lun.
1 stopDelta
9h 55mBDA-ORD
$300
5/27lun.
3 stops
29h 55mBDA-ORD
$399

Search by stops

Search by airline

Search by price

Flights to Chicago

Return flight deals:

Chicago - Bermuda

Cabin classes:

Browse origins:

Browse destinations: