$359+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
TLL — CHI
Nov 17 — Nov 241
Round-trip
1 adult, Economy
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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
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Best
Last-minute
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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 October 18, 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 October 18, 2026.
This oojo deal was found by Cheapflights users on 10/16. 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.
Thu 12/36:20 am -
1 stop18h 25m
Mon 12/77:10 pm -
2 stops16h 55m
Deal found 10/16![Scandinavian Airlines logo]()
$499
This oojo deal was found by Cheapflights users on 10/14. 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.
Thu 11/196:20 am -
1 stop18h 25m
Mon 11/237:10 pm -
2 stops16h 55m
Deal found 10/14![Scandinavian Airlines logo]()
$519
This Booking.com deal was found by Cheapflights users on 10/18. 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.
Sun 11/226:20 am -
1 stop18h 25m
Sun 11/297:10 pm -
2 stops16h 55m
Deal found 10/18![Scandinavian Airlines logo]()
$531
This Finnair deal was found by Cheapflights users on 10/17. 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.
Tue 11/105:50 am -
2 stops24h 40m
Mon 11/164:31 pm -
2 stops16h 24m
Deal found 10/17![Finnair logo]()
$542
This Booking.com deal was found by Cheapflights users on 10/17. 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.
Thu 12/35:50 am -
2 stops20h 55m
Tue 12/89:50 pm -
2 stops18h 35m
Deal found 10/17![Finnair logo]()
$555
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 October 18, 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 October 18, 2026.
This oojo deal was found by Cheapflights users on 10/16. 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.
Thu 12/36:20 am -
1 stop18h 25m
Mon 12/77:10 pm -
2 stops16h 55m
Deal found 10/16![Scandinavian Airlines logo]()
$499
This Finnair deal was found by Cheapflights users on 10/17. 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.
Tue 11/105:50 am -
2 stops24h 40m
Mon 11/164:31 pm -
2 stops16h 24m
Deal found 10/17![Finnair logo]()
$542
This oojo deal was found by Cheapflights users on 10/14. 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.
Thu 11/196:20 am -
1 stop18h 25m
Mon 11/237:10 pm -
1 stop31h 20m
Deal found 10/14![Scandinavian Airlines logo]()
$520
This Finnair deal was found by Cheapflights users on 10/18. 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.
Tue 1/1210:05 am -
2 stops17h 54m
Mon 1/251:44 pm -
2 stops16h 26m
Deal found 10/18![Finnair logo]()
$543
This oojo deal was found by Cheapflights users on 10/17. 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.
Thu 2/253:55 pm -
1 stop32h 50m
Sun 3/148:10 pm -
1 stop31h 20m
Deal found 10/17![Scandinavian Airlines logo]()
$521
This Finnair deal was found by Cheapflights users on 10/18. 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 11/55:50 am -
2 stops18h 00m
Fri 11/136:35 pm -
2 stops18h 45m
Deal found 10/18![Finnair logo]()
$581
This Scandinavian 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:20 am -
1 stop18h 25m
Tue 11/107:10 pm -
1 stop31h 20m
Deal found 10/13![Scandinavian Airlines logo]()
$610
Last-minute flights from Tallinn to ChicagoDiscover last-minute flight deals from Tallinn to Chicago. Data last updated October 18, 2026 and is based on user searches.
Discover last-minute flight deals from Tallinn to Chicago. Data last updated October 18, 2026 and is based on user searches.
This Finnair deal was found by Cheapflights users on 10/18. 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 11/55:50 am -
2 stops18h 00m
Fri 11/136:35 pm -
2 stops18h 45m
Deal found 10/18![Finnair logo]()
$581
This Scandinavian 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:20 am -
1 stop18h 25m
Tue 11/107:10 pm -
1 stop31h 20m
Deal found 10/13![Scandinavian Airlines logo]()
$610
This Finnair deal was found by Cheapflights users on 10/17. 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.
Tue 11/105:50 am -
2 stops24h 40m
Mon 11/164:31 pm -
2 stops16h 24m
Deal found 10/17![Finnair logo]()
$542
This oojo deal was found by Cheapflights users on 10/14. 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.
Thu 11/196:20 am -
1 stop18h 25m
Mon 11/237:10 pm -
2 stops16h 55m
Deal found 10/14![Scandinavian Airlines logo]()
$519
This Booking.com deal was found by Cheapflights users on 10/18. 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.
Sun 11/226:20 am -
1 stop18h 25m
Sun 11/297:10 pm -
2 stops16h 55m
Deal found 10/18![Scandinavian Airlines logo]()
$531
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 October 18, 2026.
Search for one-way flight options from Tallinn to Chicago. Find affordable one-way fares based on user searches. Data last updated October 18, 2026.
This Mytrip deal was found by Cheapflights users on 10/14. 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.
Mon 1/185:50 am -
2 stops15h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Finnair logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 1/186:30 pm -
3 stops30h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$414
This FlightHub deal was found by Cheapflights users on 10/14. 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.
Mon 1/186:55 pm -
1 stop23h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Turkish Airlines logo]()
$549
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 October 18, 2026.
Round-trip from | $499 (oojo) |
|---|---|
One-way from | $359 (Mytrip) |
Popular in | June |
Cheapest in | February |
Average price | $519 |
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 October 18, 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
Mon 1/18
5:50 am-1:45 pm
2 stops15h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$359
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Mon 1/18
6:30 pm-5:20 pm
3 stops30h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$414
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Thu 12/3
6:20 am-4:45 pm
1 stop18h 25m
Chicago O'Hare Intl
Mon 12/7
7:10 pm-8:05 pm
2 stops16h 55m
$499
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Thu 11/19
6:20 am-4:45 pm
1 stop18h 25m
Chicago O'Hare Intl
Mon 11/23
7:10 pm-10:30 am
1 stop31h 20m
$520
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Thu 2/25
3:55 pm-4:45 pm
1 stop32h 50m
Chicago O'Hare Intl
Sun 3/14
8:10 pm-10:30 am
1 stop31h 20m
$521
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Tue 11/10
5:50 am-10:30 pm
2 stops24h 40m
Chicago O'Hare Intl
Mon 11/16
4:31 pm-4:55 pm
2 stops16h 24m
$542
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Tue 1/12
10:05 am-7:59 pm
2 stops17h 54m
Chicago O'Hare Intl
Mon 1/25
1:44 pm-2:10 pm
2 stops16h 26m
$543
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Thu 11/5
5:50 am-3:50 pm
2 stops18h 00m
Chicago O'Hare Intl
Fri 11/13
6:35 pm-9:20 pm
2 stops18h 45m
$581
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Sat 11/7
6:20 am-4:45 pm
1 stop18h 25m
Chicago O'Hare Intl
Tue 11/10
7:10 pm-10:30 am
1 stop31h 20m
$610
Sorted 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 $484). 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 $497 and $629 in December.The cheapest round-trip price found within the last 5 days was $499 on Scandinavian Airlines (Dec 3-Dec 7).
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 45 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.
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Alternative routes for Tallinn to Chicago
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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 October 18, 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 October 18, 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 October 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$484 | Average$902 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$548 | Average$770 | FlexibilityNo cancel fee | On-time76% |