The cheapest times to fly from EIS to ORD are

  • January 8th to March 11th
  • April 16th to June 17th
  • September 3rd to October 21st

based on data collected exclusively by Champion Traveler across tens of millions of flights. Among all the dates above, the very cheapest time to fly from EIS to ORD is early to mid September. Prices can be as high as $1596 for Sunday flights during early January, or as low as $508 for Tuesday flights around early to mid September.


When to Fly to Chicago

Flying from Tortola (EIS) to Chicago, IL (ORD) will usually cost between $589 to $1068 per person if booking more than four weeks in advance. On average the very cheapest time to fly is early to mid September with an average ticket price of $651. Due to high demand the most expensive time to fly is early January, with an average price of $1222. Planning your trip to low-cost times can easily save you $571 on economy flights and even more on first-class flights. Generally, any price below $836 can be considered a good price for a round-trip EIS to ORD flight.

See below for a graph of average weekly prices for the EIS to ORD route. All prices are for round-trip tickets in USD.

EIS to ORD Flight Prices

Compared to other flights, the EIS to ORD flight is cheaper than the average and costs less than the average flight leaving from Tortola. The average price per mile (for a direct flight) is $0.24, which is below average.


Flight Prices by Day of the Week

Tuesday is usually the cheapest day to depart and return on this flight. Sundays are the most expensive days to fly out or take a return trip. Selecting flights on the least expensive days could save you up to $200 (21%) on this flight.

Departing prices are for round-trip flights returning on the day of departure. For example, a flight departing on Tuesday and returning a week later will cost an average of $723. Return trip prices are from the ORD to EIS flight, and often highlight the quality of our data in showing the same trend.

Departing Prices by Day

Departure Day Prices

Return Trip Prices by Day

Return Day Prices


Nonstop Flights and Layovers

Travelers looking to fly from EIS to ORD can generally find a 1-layover flight. Because there is not usually a direct flight option the real-world direct flight time of 4 hour 49 minutes may not be realistic.


Flight Hacking EIS to ORD

Flight hacking is when you book two tickets instead of a layover, sometimes with different airlines. You will need to either bring only a carry-on bag (highly recommended) or leave yourself plenty of time to go through security again. Flight hacking is completely allowed, but airlines don’t always tell you the cheapest way to get from EIS to ORD — but Champion Traveler does!

Hack #1: San Juan, PR (EIS > SJU > ORD)

  • Price for both tickets: $662
  • Average savings: $175 (20.87%)

See EIS to JFK flights

Hack #2: New York, NY (EIS > JFK > ORD)

  • Price for both tickets: $775
  • Average savings: $61 (7.3%)

See EIS to SJU flights

Hack #3: Fort Lauderdale, FL (EIS > FLL > ORD)

  • Price for both tickets: $813
  • Average savings: $24 (2.81%)

See EIS to FLL flights


Flight Questions Answered

Still have questions about flying from EIS to ORD? We’ve got answers.

Which airlines fly this route?

You can find 7 major airlines flying this route most often: American, Cape Air, Delta, JetBlue, Seaborne Airlines, Silver Airways, United, and potentially more during busy seasons.

How far away is it from Chicago O’Hare International Airport to Terrance B Lettsome Airport?

The distance between the two airports is roughly 2127 miles or 3423 kilometers.

How long does it take to fly from EIS to ORD?

The real-world flight time for a nonstop EIS to ORD flight is about 4 hour 49 minutes.

How many flights go between Tortola and Chicago, IL?

It depends on the day of the week and the date, but a typical day might have around 18 available flights from EIS to ORD.


Airport Location Info


Departing Airport

Origination code EIS
Origination airport name Terrance B Lettsome Airport
City Tortola
Country the British Virgin Islands
Latitude 18.4
Longitude -64.5

Return Airport

Destination code ORD
Destination airport name Chicago O’Hare International Airport
City Chicago, IL
Country the United States
Latitude 42
Longitude -87.9


Other Resources

Please note that while we’ve worked hard to analyzed tens of millions of flights to get you this data, we do not calculate current live prices or guarantee pricing. Please see our partners using the links above for current offers.