$285+ Cheap flights from Illinois to Road Town (EIS)
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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EIS
Nov 13 — Nov 201
1 adult, Economy
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Cheapest flights from Illinois to Road TownExplore the most affordable flight options available from Illinois to Road Town. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.
Explore the most affordable flight options available from Illinois to Road Town. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 11/288:41 amORD - EIS
1 stop7h 39mMultiple Airlines
Fri 12/54:00 pmEIS - ORD
1 stop10h 59mMultiple Airlines
Deal found 10/13![Multiple Airlines logo]()
$586
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 11/25:00 amORD - EIS
2 stops34h 20mMultiple Airlines
Sun 11/94:00 pmEIS - ORD
1 stop28h 51mMultiple Airlines
Deal found 10/12![Multiple Airlines logo]()
$682
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/275:15 amSTL - EIS
1 stop7h 45mAmerican Airlines
Thu 12/43:36 pmEIS - STL
1 stop10h 23mAmerican Airlines
Deal found 10/13![American Airlines logo]()
$844
This American Airlines deal was found by Cheapflights users on 10/13. 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.
Sat 12/135:00 amORD - EIS
1 stop10h 08mAmerican Airlines
Sat 12/2012:55 pmEIS - ORD
1 stop12h 04mAmerican Airlines
Deal found 10/13![American Airlines logo]()
$884
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Sat 11/297:30 pmORD - EIS
1 stop15h 54mAmerican Airlines
Wed 12/34:45 pmEIS - ORD
1 stop18h 04mAmerican Airlines
Deal found 10/12![American Airlines logo]()
$889
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/75:56 pmSTL - EIS
2 stops19h 12mAmerican Airlines
Sat 11/155:56 pmEIS - STL
2 stops18h 43mAmerican Airlines
Deal found 10/13![American Airlines logo]()
$1,049
Cheap flight deals from Illinois to Road Town
Keep the following information in mind while searching for Illinois to Road Town flight deals. Data was last updated October 14, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $586 (Kiwi.com) |
One-way from | $547 (American Airlines) |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Road Town 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 October 14, 2025.
Use the filters below to find and compare flights from Illinois to Road Town that are best for you.
Fly from
Illinois
Fly to
Road Town
Route
Depart
Return
Price
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Fri 11/28
8:41 am-6:20 pm
1 stop7h 39m
Road Town Beef Island
Fri 12/5
4:00 pm-12:59 am
1 stop10h 59m
$586
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Sat 1/10
5:05 am-6:20 pm
2 stops11h 15m
Road Town Beef Island
Wed 1/14
12:10 pm-6:00 pm
1 stop7h 50m
$612
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Tue 1/6
5:45 am-3:15 pm
1 stop7h 30m
Road Town Beef Island
Fri 1/16
4:00 pm-12:12 am
2 stops34h 12m
$624
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Tue 1/6
5:00 am-2:58 pm
1 stop7h 58m
Road Town Beef Island
Thu 1/15
8:00 am-4:20 pm
1 stop10h 20m
$744
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Sat 1/10
8:50 am-10:16 pm
2 stops11h 26m
Road Town Beef Island
Wed 1/14
8:00 am-6:01 pm
2 stops12h 01m
$794
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Tue 3/3
2:20 pm-6:30 pm
1 stop26h 10m
Road Town Beef Island
Fri 3/6
8:15 am-11:57 am
1 stop29h 42m
$815
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Sun 3/1
10:07 am-9:55 pm
1 stop9h 48m
Road Town Beef Island
Sat 3/7
8:00 am-11:18 pm
1 stop17h 18m
$834
St. LouisRoad Town
STL - EIS
STLEIS
Lambert-St Louis
Thu 11/27
5:15 am-3:00 pm
1 stop7h 45m
Road Town Beef Island
Thu 12/4
3:36 pm-11:59 pm
1 stop10h 23m
$844
St. LouisRoad Town
STL - EIS
STLEIS
Lambert-St Louis
Fri 11/7
5:56 pm-3:08 pm
2 stops19h 12m
Road Town Beef Island
Sat 11/15
5:56 pm-10:39 am
2 stops18h 43m
$1,049
ChicagoRoad Town
ORD - EIS
ORDEIS
Chicago O'Hare Intl
Sat 1/31
5:05 am-6:20 pm
2 stops11h 15m
$285
Showing 1-10 of 13 results
Best time to book a flight from Illinois to Road Town
Have a flexible travel schedule? Discover the best time to fly to Road Town from Illinois with our price prediction graph.
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 Illinois to Road Town
What is the cheapest time of day to fly from IL to EIS?
Find hourly flight availability from Illinois to Road Town. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 14, 2025.
When flying from Illinois to Road Town, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 9% versus a flight at noon.
Related info for your journey
Find useful and relevant information for your journey from Illinois to Road Town. 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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Alternative routes for Illinois to Road Town
See prices for flight routes from nearby airports that may be better suited for you.
Top 2 airlines flying from Illinois to Road Town
Discover the top 2 airlines that operate flights from Illinois to Road Town. 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 October 14, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$693 | Average$873 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$747 | Average$952 | FlexibilityNo cancel fee | On-time69% |