$321+ Cheap flights from Tallinn (TLL) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
TLL — CHI
Oct 10 — Oct 171
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Tallinn to Chicago 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 Tallinn to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Tallinn to ChicagoExplore the most affordable flight options available from Tallinn to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
Explore the most affordable flight options available from Tallinn to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
This Booking.com deal was found by Cheapflights users on 9/6. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:20 pm -
1 stop32h 50m
Wed 10/2810:50 pm -
1 stop31h 35m
Deal found 9/6![LOT logo]()
$553
This oojo deal was found by Cheapflights users on 9/5. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:35 pm -
2 stops28h 10m
Fri 10/308:15 pm -
1 stop12h 05m
Deal found 9/5![Scandinavian Airlines logo]()
$563
This Scandinavian Airlines deal was found by Cheapflights users on 9/6. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:25 am -
1 stop18h 20m
Tue 11/37:15 pm -
2 stops20h 50m
Deal found 9/6![Scandinavian Airlines logo]()
$570
This Expedia deal was found by Cheapflights users on 9/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:25 am -
1 stop18h 25m
Wed 10/284:25 pm -
2 stops17h 30m
Deal found 9/6![Finnair logo]()
$571
This LOT deal was found by Cheapflights users on 9/6. 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 LOT is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:05 pm -
1 stop13h 50m
Tue 11/39:50 pm -
1 stop31h 35m
Deal found 9/6![LOT logo]()
$592
This Finnair deal was found by Cheapflights users on 9/7. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:15 pm -
2 stops23h 45m
Thu 10/2910:30 pm -
2 stops16h 45m
Deal found 9/7![Finnair logo]()
$599
Best flights from Tallinn to ChicagoDiscover carefully curated flight deals from Tallinn to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
Discover carefully curated flight deals from Tallinn to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
This Booking.com deal was found by Cheapflights users on 9/6. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:20 pm -
1 stop32h 50m
Wed 10/2810:50 pm -
1 stop31h 35m
Deal found 9/6![LOT logo]()
$553
This oojo deal was found by Cheapflights users on 9/5. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:35 pm -
2 stops28h 10m
Fri 10/308:15 pm -
1 stop12h 05m
Deal found 9/5![Scandinavian Airlines logo]()
$563
This Expedia deal was found by Cheapflights users on 9/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:25 am -
1 stop18h 25m
Wed 10/284:25 pm -
2 stops17h 30m
Deal found 9/6![Finnair logo]()
$571
This Scandinavian Airlines deal was found by Cheapflights users on 9/6. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:25 am -
1 stop18h 20m
Tue 11/37:15 pm -
2 stops20h 50m
Deal found 9/6![Scandinavian Airlines logo]()
$570
This Finnair deal was found by Cheapflights users on 9/7. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:15 pm -
2 stops23h 45m
Thu 10/2910:25 pm -
1 stop16h 50m
Deal found 9/7![Finnair logo]()
$607
Last-minute flights from Tallinn to ChicagoDiscover last-minute flight deals from Tallinn to Chicago. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Tallinn to Chicago. Data last updated September 10, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 9/6. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:20 pm -
1 stop32h 50m
Wed 10/2810:50 pm -
1 stop31h 35m
Deal found 9/6![LOT logo]()
$553
This Expedia deal was found by Cheapflights users on 9/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:25 am -
1 stop18h 25m
Wed 10/284:25 pm -
2 stops17h 30m
Deal found 9/6![Finnair logo]()
$571
This Finnair deal was found by Cheapflights users on 9/7. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:15 pm -
2 stops23h 45m
Thu 10/2910:30 pm -
2 stops16h 45m
Deal found 9/7![Finnair logo]()
$599
This oojo deal was found by Cheapflights users on 9/5. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:35 pm -
2 stops28h 10m
Fri 10/308:15 pm -
1 stop12h 05m
Deal found 9/5![Scandinavian Airlines logo]()
$563
This Scandinavian Airlines deal was found by Cheapflights users on 9/6. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:25 am -
1 stop18h 20m
Tue 11/37:15 pm -
2 stops20h 50m
Deal found 9/6![Scandinavian Airlines logo]()
$570
This LOT deal was found by Cheapflights users on 9/6. 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 LOT is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:05 pm -
1 stop13h 50m
Tue 11/39:50 pm -
1 stop31h 35m
Deal found 9/6![LOT logo]()
$592
One-way flights from Tallinn to ChicagoSearch for one-way flight options from Tallinn to Chicago. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
Search for one-way flight options from Tallinn to Chicago. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Mytrip deal was found by Cheapflights users on 9/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:40 pm -
2 stops28h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Finnair logo]()
$321
This Travelocity deal was found by Cheapflights users on 9/8. 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 11/12:35 pm -
2 stops15h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Finnair logo]()
$330
This FlightHub deal was found by Cheapflights users on 9/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:50 am -
2 stops23h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![British Airways logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 12/189:30 am -
2 stops15h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Mon 12/79:30 am -
2 stops15h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$396
This FlightHub deal was found by Cheapflights users on 9/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:25 am -
1 stop18h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Scandinavian Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 9/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:35 pm -
2 stops40h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Sun 12/208:30 am -
3 stops40h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$428
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Sat 12/53:55 pm -
1 stop32h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Scandinavian Airlines logo]()
$433
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 12/29:40 am -
3 stops39h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$438
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Fri 12/49:45 am -
3 stops39h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Tue 12/85:50 am -
3 stops51h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$444
Find flight deals from Tallinn to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Tallinn (TLL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 10, 2026.
Round-trip from | $553 (Booking.com) |
|---|---|
One-way from | $321 (Mytrip) |
Popular in | June |
Cheapest in | April |
Average price | $538 |
Cheapflights Fare Finder
Customize your flight search to find flights from Tallinn to Chicago 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 7,457,451 searches. Data last updated September 10, 2026.
Use the filters below to find and compare flights from Tallinn to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Sun 11/1
2:35 pm-10:30 pm
2 stops15h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$330
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Fri 12/4
5:50 am-9:12 pm
2 stops23h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$339
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Wed 12/2
2:35 pm-11:00 pm
2 stops40h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$426
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Tue 12/8
5:50 am-11:59 pm
2 stops26h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$426
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Thu 12/3
4:30 pm-10:15 pm
2 stops37h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$426
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Sun 12/20
8:30 am-5:20 pm
3 stops40h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$428
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Sat 12/5
3:55 pm-4:45 pm
1 stop32h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$433
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Tue 12/8
3:55 pm-4:45 pm
1 stop32h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$433
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Wed 12/16
8:55 pm-3:30 pm
2 stops50h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$470
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Fri 12/18
6:25 am-5:20 pm
3 stops18h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$514
Showing 1-10 of 16 resultsSorted by cheapest first
Best time to book a flight from Tallinn to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Tallinn with our price prediction graph.
TLL-CHI
TLL-ORD
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 Tallinn to Chicago
TLL-CHI
TLL-ORD
What is the cheapest month to book a flight from Tallinn to Chicago?
Currently, April is the cheapest month in which you can book a flight from Tallinn to Chicago (average of $458). Flying from Tallinn to Chicago in June is currently the most expensive (average of $880). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Tallinn to Chicago?
Airfare is typical for this route at the moment.
Tallinn to Chicago flights typically cost between $468 and $596 in October.The cheapest round-trip price found within the last 5 days was $553 on LOT (Oct 21-Oct 28).
How far ahead should I book a flight from Tallinn to Chicago?
To ensure you get the cheapest price possible for a flight from Tallinn to Chicago, you should look to book at least 73 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Related info for your journey
Find useful and relevant information for your journey from Tallinn to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Tallinn to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 10, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Tallinn to Chicago by cabin class
Find flights from Tallinn to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Tallinn and Chicago flights
Browse other Tallinn and Chicago flight options. Last updated on September 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Tallinn to Chicago
Discover the top 2 airlines that operate flights from Tallinn to Chicago. 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 7,457,451 searches. Data last updated September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$484 | Average$789 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$548 | Average$770 | FlexibilityNo cancel fee | On-time76% |