$348+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EIS
Jul 9 — Jul 161
Round-trip
1 adult, Economy
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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
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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
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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 June 9, 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 June 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 8/1012:44 am
ORD
- EIS
1 stop12h 21m
Multiple Airlines
Tue 8/184:00 pm
EIS
- ORD
2 stops45h 25m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$598
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/1812:44 am
ORD
- EIS
1 stop12h 21m
Multiple Airlines
Sun 7/269:00 am
EIS
- ORD
1 stop15h 27m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$706
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Wed 8/512:44 am
ORD
- EIS
1 stop9h 11m
Multiple Airlines
Sat 8/159:00 am
EIS
- ORD
2 stops15h 10m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$718
This Trip.com deal was found by Cheapflights users on 6/7. 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.
Fri 7/1012:44 am
ORD
- EIS
1 stop16h 26m
Multiple Airlines
Sat 7/189:00 am
EIS
- ORD
1 stop15h 27m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$725
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/712:44 am
ORD
- EIS
1 stop12h 21m
Multiple Airlines
Wed 7/159:00 am
EIS
- ORD
1 stop15h 27m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$728
This Travelocity deal was found by Cheapflights users on 6/8. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:00 am
ORD
- EIS
3 stops12h 45m
Multiple Airlines
Sun 9/277:15 am
EIS
- ORD
3 stops17h 16m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$749
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/612:44 am
ORD
- EIS
1 stop12h 21m
Multiple Airlines
Mon 7/134:00 pm
EIS
- ORD
2 stops45h 15m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$757
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 7/315:13 pm
ORD
- EIS
2 stops16h 42m
Multiple Airlines
Fri 8/74:00 pm
EIS
- ORD
1 stop8h 27m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$778
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 June 9, 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 June 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/1812:44 am
ORD
- EIS
1 stop12h 21m
Multiple Airlines
Sun 7/269:00 am
EIS
- ORD
1 stop15h 27m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$706
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Thu 6/259:52 am
ORD
- EIS
2 stops11h 06m
American Airlines
Thu 7/25:06 pm
EIS
- ORD
1 stop8h 20m
American Airlines
Deal found 6/8![American Airlines logo]()
$905
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Mon 8/102:38 pm
ORD
- EIS
1 stop27h 22m
United Airlines
Thu 8/1312:20 pm
EIS
- ORD
1 stop8h 45m
United Airlines
Deal found 6/8![United Airlines logo]()
$940
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 7/315:13 pm
ORD
- EIS
2 stops16h 42m
Multiple Airlines
Fri 8/74:00 pm
EIS
- ORD
1 stop8h 27m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$778
This American Airlines deal was found by Cheapflights users on 6/5. 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.
Wed 6/248:00 am
ORD
- EIS
2 stops12h 58m
American Airlines
Wed 7/15:12 pm
EIS
- ORD
1 stop16h 56m
American Airlines
Deal found 6/5![American Airlines logo]()
$1,000
Last-minute flights from Chicago to TortolaDiscover last-minute flight deals from Chicago to Tortola. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Tortola. Data last updated June 9, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 6/297:52 am
ORD
- EIS
2 stops9h 18m
Multiple Airlines
Fri 7/34:00 pm
EIS
- ORD
1 stop8h 29m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$798
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/612:44 am
ORD
- EIS
1 stop12h 21m
Multiple Airlines
Mon 7/134:00 pm
EIS
- ORD
2 stops45h 15m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$757
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/712:44 am
ORD
- EIS
1 stop12h 21m
Multiple Airlines
Wed 7/159:00 am
EIS
- ORD
1 stop15h 27m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$728
This Trip.com deal was found by Cheapflights users on 6/7. 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.
Fri 7/1012:44 am
ORD
- EIS
1 stop16h 26m
Multiple Airlines
Sat 7/189:00 am
EIS
- ORD
1 stop15h 27m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$725
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/1812:44 am
ORD
- EIS
1 stop12h 21m
Multiple Airlines
Sun 7/269:00 am
EIS
- ORD
1 stop15h 27m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$706
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 7/315:13 pm
ORD
- EIS
2 stops16h 42m
Multiple Airlines
Fri 8/74:00 pm
EIS
- ORD
1 stop8h 27m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$778
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 June 9, 2026.
Search for one-way flight options from Chicago to Tortola. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
Wed 7/2912:44 am
ORD
- EIS
1 stop9h 11m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/2412:44 am
ORD
- EIS
1 stop12h 21m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/235:13 pm
ORD
- EIS
2 stops23h 57m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$381
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
Wed 7/229:57 pm
ORD
- EIS
3 stops43h 13m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$413
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Thu 7/236:59 am
ORD
- EIS
1 stop8h 27m
American Airlines
Deal found 6/8![American Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Wed 7/228:30 am
ORD
- EIS
2 stops12h 19m
American Airlines
Deal found 6/8![American Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/2512:11 pm
MDW
- EIS
3 stops24h 54m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/306:05 am
MDW
- EIS
3 stops27h 50m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/2312:11 pm
MDW
- EIS
3 stops28h 59m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$479
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
Wed 7/2212:11 pm
MDW
- EIS
3 stops50h 24m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$640
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 June 9, 2026.
Round-trip from | $598 (Kiwi.com) |
|---|---|
One-way from | $348 (Kiwi.com) |
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 June 9, 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
Cheapest round-trip
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Sat 7/18
12:44 am-2:05 pm
1 stop12h 21m
Road Town Beef Island
Sun 7/26
9:00 am-11:27 pm
1 stop15h 27m
$706
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Fri 7/31
5:13 pm-10:55 am
2 stops16h 42m
Road Town Beef Island
Fri 8/7
4:00 pm-11:27 pm
1 stop8h 27m
$778
Quickest round-trip
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Thu 6/25
9:52 am-9:58 pm
2 stops11h 06m
Road Town Beef Island
Thu 7/2
5:06 pm-12:26 am
1 stop8h 20m
$905
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Mon 8/10
2:38 pm-7:00 pm
1 stop27h 22m
Road Town Beef Island
Thu 8/13
12:20 pm-8:05 pm
1 stop8h 45m
$940
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Wed 6/24
8:00 am-9:58 pm
2 stops12h 58m
Road Town Beef Island
Wed 7/1
5:12 pm-9:08 am
1 stop16h 56m
$1,000
Cheapest one-way
Quickest one-way
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Wed 7/29
12:44 am-10:55 am
1 stop9h 11m
$348
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Sat 7/25
5:13 pm-2:05 pm
2 stops19h 52m
$382
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Wed 7/22
8:30 am-9:49 pm
2 stops12h 19m
$423
ChicagoRoad Town
MDW - EIS
MDWEIS
Chicago Midway
Thu 7/23
12:11 pm-6:10 pm
3 stops28h 59m
$479
ChicagoRoad Town
MDW - EIS
MDWEIS
Chicago Midway
Wed 7/22
12:11 pm-3:35 pm
3 stops50h 24m
$640
Sorted 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 June 9, 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.
Boarding
7.5
Entertainment
6.9
Food
6.4
Overall
7.1
Crew
7.9
Comfort
7.2
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Boarding
7.5
Entertainment
6.9
Food
6.4
Overall
7.1
Crew
7.9
Comfort
7.2
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
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.
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Other flight options
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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 June 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Chicago to Tortola
Discover the top airline 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 June 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$693 | Average$908 | FlexibilityNo cancel fee | On-time71% |