$235+ Cheap flights from Chicago (CHI) to Tortola
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EIS
Apr 2 — Apr 91
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Tortola with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Tortola
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to TortolaExplore the most affordable flight options available from Chicago to Tortola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 3, 2026.
Explore the most affordable flight options available from Chicago to Tortola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 3, 2026.
This Trip.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/810:55 am
ORD
- EIS
2 stops26h 10m
Multiple Airlines
Mon 4/134:00 pm
EIS
- ORD
2 stops27h 31m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$506
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/193:08 pm
ORD
- EIS
2 stops21h 57m
Multiple Airlines
Tue 4/2811:35 am
EIS
- ORD
1 stop28h 33m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$536
This Kiwi.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/74:21 pm
ORD
- EIS
2 stops20h 44m
Multiple Airlines
Thu 4/1611:35 am
EIS
- ORD
1 stop10h 14m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$554
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:56 pm
ORD
- EIS
1 stop12h 59m
Multiple Airlines
Fri 4/174:00 pm
EIS
- ORD
2 stops31h 39m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$560
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:05 pm
ORD
- EIS
2 stops41h 10m
Multiple Airlines
Tue 3/1712:10 pm
EIS
- ORD
1 stop18h 35m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$561
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/128:56 pm
ORD
- EIS
1 stop16h 09m
Multiple Airlines
Sun 4/194:00 pm
EIS
- ORD
2 stops34h 09m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$562
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/148:56 pm
ORD
- EIS
1 stop12h 59m
Multiple Airlines
Tue 4/214:00 pm
EIS
- ORD
1 stop24h 08m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$564
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:56 pm
ORD
- EIS
1 stop12h 59m
Multiple Airlines
Sat 4/184:00 pm
EIS
- ORD
2 stops22h 32m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$566
This Kiwi.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/78:56 pm
ORD
- EIS
1 stop12h 59m
Multiple Airlines
Wed 4/154:00 pm
EIS
- ORD
1 stop29h 49m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$574
Best flights from Chicago to TortolaDiscover carefully curated flight deals from Chicago to Tortola that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 3, 2026.
Discover carefully curated flight deals from Chicago to Tortola that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 3, 2026.
This Trip.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/810:55 am
ORD
- EIS
2 stops26h 10m
Multiple Airlines
Mon 4/134:00 pm
EIS
- ORD
2 stops27h 31m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$506
This American Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:00 am
ORD
- EIS
1 stop15h 58m
American Airlines
Thu 6/118:19 am
EIS
- ORD
1 stop9h 55m
American Airlines
Deal found 3/1![American Airlines logo]()
$768
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/219:30 am
ORD
- EIS
1 stop22h 45m
United Airlines
Sat 3/283:00 pm
EIS
- ORD
1 stop28h 44m
United Airlines
Deal found 3/1![United Airlines logo]()
$1,038
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:05 am
ORD
- EIS
2 stops28h 50m
Multiple Airlines
Thu 6/114:00 pm
EIS
- ORD
1 stop9h 25m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$587
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1512:59 am
ORD
- EIS
1 stop12h 06m
Multiple Airlines
Sat 8/229:00 am
EIS
- ORD
1 stop16h 25m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$590
This United Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/292:38 pm
ORD
- EIS
1 stop26h 52m
United Airlines
Sun 4/59:41 am
EIS
- ORD
1 stop27h 12m
United Airlines
Deal found 2/26![United Airlines logo]()
$1,086
Last-minute flights from Chicago to TortolaDiscover last-minute flight deals from Chicago to Tortola. Data last updated March 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Tortola. Data last updated March 3, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:05 pm
ORD
- EIS
2 stops41h 10m
Multiple Airlines
Tue 3/1712:10 pm
EIS
- ORD
1 stop18h 35m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$561
This Kiwi.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/78:56 pm
ORD
- EIS
1 stop16h 09m
Multiple Airlines
Wed 4/154:00 pm
EIS
- ORD
2 stops24h 08m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$554
This Trip.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/810:55 am
ORD
- EIS
2 stops26h 10m
Multiple Airlines
Mon 4/134:00 pm
EIS
- ORD
2 stops27h 31m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$506
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:56 pm
ORD
- EIS
1 stop12h 59m
Multiple Airlines
Fri 4/174:00 pm
EIS
- ORD
2 stops31h 39m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$560
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:56 pm
ORD
- EIS
1 stop12h 59m
Multiple Airlines
Sat 4/184:00 pm
EIS
- ORD
2 stops22h 32m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$566
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/128:56 pm
ORD
- EIS
1 stop16h 09m
Multiple Airlines
Sun 4/194:00 pm
EIS
- ORD
2 stops34h 09m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$562
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/148:56 pm
ORD
- EIS
1 stop12h 59m
Multiple Airlines
Tue 4/214:00 pm
EIS
- ORD
1 stop24h 08m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$564
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/193:08 pm
ORD
- EIS
2 stops21h 57m
Multiple Airlines
Tue 4/2811:35 am
EIS
- ORD
1 stop28h 33m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$536
One-way flights from Chicago to TortolaSearch for one-way flight options from Chicago to Tortola. Find affordable one-way fares based on user searches. Data last updated March 3, 2026.
Search for one-way flight options from Chicago to Tortola. Find affordable one-way fares based on user searches. Data last updated March 3, 2026.
This Mytrip deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- EIS
2 stops23h 00m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/314:18 pm
ORD
- EIS
2 stops24h 52m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$240
This Mytrip deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/148:56 pm
ORD
- EIS
1 stop12h 59m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:52 pm
ORD
- EIS
3 stops42h 03m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:09 pm
MDW
- EIS
3 stops41h 46m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:00 am
MDW
- EIS
2 stops11h 10m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:30 am
MDW
- EIS
3 stops29h 35m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$356
Find flight deals from Chicago to Tortola
Keep the following information in mind while searching for Chicago to Tortola flight deals. Data was last updated March 3, 2026.
Round-trip from | $536 (Kiwi.com) |
|---|---|
One-way from | $235 (Mytrip) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Tortola that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 3, 2026.
Use the filters below to find and compare flights from Chicago to Tortola that are best for you.
Fly from
Fly to
Route
Depart
Return
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Wed 4/8
10:55 am-2:05 pm
2 stops26h 10m
Road Town Beef Island
Mon 4/13
4:00 pm-6:31 pm
2 stops27h 31m
$506
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Sat 6/6
5:05 am-10:55 am
2 stops28h 50m
Road Town Beef Island
Thu 6/11
4:00 pm-12:25 am
1 stop9h 25m
$587
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Sat 8/15
12:59 am-2:05 pm
1 stop12h 06m
Road Town Beef Island
Sat 8/22
9:00 am-12:25 am
1 stop16h 25m
$590
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Fri 6/5
5:00 am-9:58 pm
1 stop15h 58m
Road Town Beef Island
Thu 6/11
8:19 am-5:14 pm
1 stop9h 55m
$768
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Sat 3/21
9:30 am-9:15 am
1 stop22h 45m
Road Town Beef Island
Sat 3/28
3:00 pm-6:44 pm
1 stop28h 44m
$1,038
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Sun 3/29
2:38 pm-6:30 pm
1 stop26h 52m
Road Town Beef Island
Sun 4/5
9:41 am-11:53 am
1 stop27h 12m
$1,086
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Tue 4/7
10:55 am-10:55 am
2 stops23h 00m
$235
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Tue 3/31
4:18 pm-6:10 pm
2 stops24h 52m
$240
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Thu 5/7
7:50 am-6:10 pm
2 stops33h 20m
$240
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Tue 4/14
8:56 pm-10:55 am
1 stop12h 59m
$256
Showing 1-10 of 16 resultsSorted by cheapest first
Best time to book a flight from Chicago to Tortola
Have a flexible travel schedule? Discover the best time to fly to Tortola from Chicago with our price prediction graph.
ORD-EIS
MDW-EIS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Tortola
CHI-zzLNS
ORD-EIS
MDW-EIS
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Tortola
Get insights into the airlines that provide service to Tortola. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Tortola. Reviews last updated March 3, 2026.
Read through reviews of airlines operating flights from Chicago to Tortola, such as American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.4
Entertainment
6.9
Overall
7.1
Comfort
7.2
Crew
8.0
Boarding
7.5
Reviews
1 / 20
2.0
MediocreSusie,Jan 2026
CLT - TPA
Food
6.4
Entertainment
6.9
Overall
7.1
Comfort
7.2
Crew
8.0
Boarding
7.5
Reviews
1 / 20
2.0
MediocreSusie,Jan 2026
CLT - TPA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Tortola. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Complete your trip
Complete your trip to Tortola by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Tortola by cabin class
Find flights from Chicago to Tortola, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Tortola flights
Browse other Chicago and Tortola flight options. Last updated on March 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Tortola
Discover the top 2 airlines that operate flights from Chicago to Tortola. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$693 | Average$894 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$747 | Average$972 | FlexibilityNo cancel fee | On-time69% |