Chicago, Vancouver, Toronto, & More: €326 Icelandair Flights from Dublin (Iceland Stopover Possible; €466 with Luggage)

Chicago Willis Tower Skydeck city architecture and skyscrapers near waterfront

You can currently fly to 5 North American destinations from Dublin for as little as €326, thanks to an Icelandair sale. Not only is this a low price, but the fare also allows you to add a free stopover in Iceland. The availability is highest in the winter, but there are also some dates in early Spring. The fare includes 10 kg of hand luggage. Should you want to fly with a 23 kg piece of checked luggage, that will raise the price by €125 – €140, depending on the route.

You can fly to:

Our calendar displays all available dates and can redirect you to either Trip.com or Icelandair’s website. Both have similar prices, but Trip.com is usually ~€15 cheaper if you want to fly with luggage. Feel free to always check both options.

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You will always first fly to Reykjavik, and then continue onward to North America after a short layover. Icelandair uses a Boeing 737 MAX for most flights, and sometimes a Boeing 767 (e.g. to Boston).

Visa Info

Most Europeans need an electronic system for travel authorization (ESTA) to enter the USA for up to 90 days. This costs US$40 (~€34) and you should apply for it a couple of days before your trip, at the latest.

There are some cases where you cannot apply for an ESTA, e.g. if you’ve been to Cuba since 2021 or to Iran, Iraq, Syria, Sudan, or North Korea since March 2011. In those cases, you’ll need to get a visa from a US embassy or consulate, which can take multiple weeks.

Most European passport holders can stay in Canada for up to 180 days, but you must obtain an electronic travel authorization before your arrival in the country

Search & Book

This sale will end on December 2, 2025 and is valid for trips that end before March 15, 2026. The minimum stay requirement is 3 days. You can find all available dates on Google Flights. You can then either book directly on Icelandair’s website or Trip.com. Icelandair’s website is better if you want to add a stopover, Trip.com is cheaper if you want to fly with checked luggage.

Iceland Stopover

On Icelandair’s website, you have the option to use Stopover in Iceland for a layover in Iceland either on the outbound or inbound journey, allowing for a city break in Reykjavik. The price depends on your dates and may be slightly more expensive than a standard return ticket, but it offers the opportunity to have a stopover in Iceland en route.

Here is one example:

Miles & Points

The tickets are issued in booking class X. You only option (outside the Saga Club) is Alaska Airlines’ Mileage Plan, where a round trip will earn you roughly 2,500 miles.

Destination

Information & Tips for Chicago

Chicago is known for its architecture, museums, and lakefront, with highlights like Millennium Park, the Art Institute of Chicago, and the Willis Tower. The currency is the U.S. dollar (USD), and credit cards are widely accepted. Prices can be high, especially for accommodation and dining in central areas, though there are budget options. The weather is variable—summers are warm and humid, winters are cold with snow, and spring and fall are unpredictable, so packing layers is advised.

Climate diagram for Chicago, Illinois (Source: WMO World Weather Information Service)

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The Best eSIM Plans for the USA 🇺🇸 Compared

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Information & Tips for Vancouver

Vancouver is known for its stunning natural surroundings, including Stanley Park, Granville Island, and nearby mountains like Grouse Mountain, which offer year-round outdoor activities. The currency used is the Canadian dollar (CAD), and credit cards are widely accepted. The city is generally on the expensive side, with higher prices for accommodation and dining, especially in tourist areas. Vancouver has a mild, oceanic climate, with cool, wet winters and mild summers, making it an attractive year-round destination, although the weather can be unpredictable, especially in the winter.

Climate diagram for Vancouver, British Columbia (Source: WMO World Weather Information Service)

We’ve compared various esim providers, such as Airalo and Maya Mobile. To see which plan is best for your travel needs and which network offers the best coverage, feel free to read our detailed guide:

The Best eSIM Plans for Canada 🇨🇦 Compared

→ All Dealz for Vancouver

Information & Tips for Toronto

Toronto is known for its iconic CN Tower, diverse neighbourhoods like Kensington Market, and attractions such as the Royal Ontario Museum and nearby Niagara Falls. The currency is the Canadian dollar (CAD), and credit cards are widely accepted. The price level can be high, especially in terms of accommodation and dining in central areas, but there are budget options available. Toronto experiences cold winters with snow and mild, humid summers, making the best times to visit spring and fall when temperatures are more moderate.

Climate diagram for Toronto, Ontario (Source: WMO World Weather Information Service)

We’ve compared various esim providers, such as Airalo and Maya Mobile. To see which plan is best for your travel needs and which network offers the best coverage, feel free to read our detailed guide:

The Best eSIM Plans for Canada 🇨🇦 Compared

 

→ All Dealz for Toronto

Information & Tips for Baltimore

Baltimore’s main draw is its waterfront Inner Harbor, home to the National Aquarium, historic ships, and easy access to neighborhoods like Fells Point and Mount Vernon. The currency is the US dollar (USD), and cards are accepted almost everywhere. Prices are moderate by U.S. standards—lower than New York or Washington, D.C., but still not cheap, especially for hotels near the harbor. Weather varies widely: summers are hot and humid, winters can be cold with occasional snow, and spring and fall tend to be the most comfortable times for exploring.

Climate diagram for Baltimore, Maryland (Source: WMO World Weather Information Service)

We’ve compared various esim providers, such as Knowroaming and Ubigi. To see which plan is best for your travel needs and which network offers the best coverage, feel free to read our detailed guide:

The Best eSIM Plans for the USA 🇺🇸 Compared

→ All Dealz for Baltimore

Information & Tips for Boston

Boston is known for its historic landmarks like the Freedom Trail, Boston Common, and Harvard University across the river in Cambridge. The local currency is the U.S. dollar (USD), and prices are relatively high, especially for accommodation and dining. The city has four distinct seasons—winters can be cold and snowy, while summers are warm and humid. Spring and fall are milder and popular times to visit.

Climate diagram for Boston, Massachusetts (Source: WMO World Weather Information Service)

We’ve compared various esim providers, such as Knowroaming and Ubigi. To see which plan is best for your travel needs and which network offers the best coverage, feel free to read our detailed guide:

The Best eSIM Plans for the USA 🇺🇸 Compared

→ All Dealz for Boston

Cover Picture: Photo by Pedro Lastra on Unsplash

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