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Tallinn

$255+ Cheap flights from Chicago (CHI) to Tallinn (TLL)

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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TLL
Feb 18 — Feb 251
Wed 2/18
Wed 2/25
1 adult, Economy
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Cheap flight deals from Chicago to Tallinn

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Tallinn (TLL). 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 January 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$440
(oojo)

One-way from

$255
(American Airlines)

Popular in

September

Cheapest in

February

Average price

$593
Provider with most accurate pricing for Chicago (CHI)-Tallinn flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Tallinn flights.
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From Chicago (CHI) to Tallinn
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One-way flight from Chicago (CHI) to Tallinn
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Highest demand for flights based on searches. 6% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Chicago to Tallinn

Cheapest flights from Chicago to Tallinn
Explore the most affordable flight options available from Chicago to Tallinn. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 19, 2026.

This oojo deal was found by Cheapflights users on 1/17. 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.
Fri 2/67:20 pm
ORD
-
TLL
1 stop31h 00m
Scandinavian Airlines
Sat 2/1411:00 am
TLL
-
ORD
1 stop13h 45m
Scandinavian Airlines
Deal found 1/17$440
This oojo deal was found by Cheapflights users on 1/17. 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.
Sun 3/88:20 pm
ORD
-
TLL
1 stop11h 50m
Scandinavian Airlines
Sun 3/154:10 pm
TLL
-
ORD
2 stops32h 35m
Scandinavian Airlines
Deal found 1/17$441
This Kiwi.com deal was found by Cheapflights users on 1/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/39:55 pm
ORD
-
TLL
1 stop31h 30m
LOT
Tue 3/102:05 pm
TLL
-
ORD
1 stop13h 55m
LOT
Deal found 1/17$460
This oojo deal was found by Cheapflights users on 1/17. 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.
Sun 4/269:50 pm
ORD
-
TLL
1 stop11h 55m
LOT
Sun 5/32:20 pm
TLL
-
ORD
1 stop13h 30m
LOT
Deal found 1/17$462
This Mytrip deal was found by Cheapflights users on 1/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/34:05 pm
ORD
-
TLL
1 stop16h 45m
Multiple Airlines
Tue 3/107:25 am
TLL
-
ORD
2 stops17h 23m
Multiple Airlines
Deal found 1/17$475
This FlightHub deal was found by Cheapflights users on 1/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:15 pm
ORD
-
TLL
2 stops31h 50m
Scandinavian Airlines
Sun 9/133:50 pm
TLL
-
ORD
1 stop32h 20m
Scandinavian Airlines
Deal found 1/18$478
This oojo deal was found by Cheapflights users on 1/17. 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.
Mon 9/75:10 pm
ORD
-
TLL
1 stop12h 30m
LOT
Sun 9/135:45 am
TLL
-
ORD
1 stop22h 05m
LOT
Deal found 1/17$490
This Finnair deal was found by Cheapflights users on 1/17. 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 3/36:30 pm
ORD
-
TLL
2 stops19h 25m
Finnair
Tue 3/108:25 am
TLL
-
ORD
2 stops28h 00m
Finnair
Deal found 1/17$492

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Tallinn 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 January 19, 2026.
Use the filters below to find and compare flights from Chicago to Tallinn that are best for you.

Fly from

Chicago

Fly to

Tallinn

Route

Depart

Return

Price

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Fri 2/6

7:20 pm-10:20 am

1 stop31h 00m

Tallinn

Sat 2/14

11:00 am-4:45 pm

1 stop13h 45m

$440

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Sun 3/8

8:20 pm-3:10 pm

1 stop11h 50m

Tallinn

Sun 3/15

4:10 pm-5:45 pm

2 stops32h 35m

$441

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Tue 3/3

9:55 pm-1:25 pm

1 stop31h 30m

Tallinn

Tue 3/10

2:05 pm-9:00 pm

1 stop13h 55m

$460

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Sun 4/26

9:50 pm-5:45 pm

1 stop11h 55m

Tallinn

Sun 5/3

2:20 pm-7:50 pm

1 stop13h 30m

$462

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Tue 3/3

4:05 pm-4:50 pm

1 stop16h 45m

Tallinn

Tue 3/10

7:25 am-5:48 pm

2 stops17h 23m

$475

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Tue 5/19

9:30 pm-3:45 pm

1 stop10h 15m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/17

Compare providers for flights from Chicago to Tallinn

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Tallinn in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Tallinn flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Tallinn flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Tallinn flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Tallinn flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Tallinn flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Tallinn

Have a flexible travel schedule? Discover the best time to fly to Tallinn from Chicago 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 Chicago to Tallinn

What is the cheapest month to book a flight from Chicago to Tallinn?

Currently, April is the cheapest month in which you can book a flight from Chicago to Tallinn (average of $431). Flying from Chicago to Tallinn in July is currently the most expensive (average of $808). 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 Chicago to Tallinn?

Reviews of airlines servicing Tallinn

Get insights into the airlines that provide service to Tallinn. 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 Tallinn. Reviews last updated January 19, 2026.
Read through reviews of airlines operating flights from Chicago to Tallinn, such as Finnair, United Airlines, and Scandinavian Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Finnair
7.6
Good
1,351 reviews

Comfort

7.4

Boarding

7.7

Entertainment

6.9

Overall

7.6

Crew

8.2

Food

6.7

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.
Finnair
7.6
Good
1,351 reviews
Finnair
7.6
Good
1,351 reviews

Comfort

7.4

Boarding

7.7

Entertainment

6.9

Overall

7.6

Crew

8.2

Food

6.7

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.
United Airlines
7.4
Good
9,176 reviews
Finnair
7.6
Good
1,351 reviews

Comfort

7.4

Boarding

7.7

Entertainment

6.9

Overall

7.6

Crew

8.2

Food

6.7

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.
Scandinavian Airlines
7.3
Good
1,655 reviews
Finnair
7.6
Good
1,351 reviews

Comfort

7.4

Boarding

7.7

Entertainment

6.9

Overall

7.6

Crew

8.2

Food

6.7

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.
Lufthansa
6.8
Okay
7,731 reviews
Finnair
7.6
Good
1,351 reviews

Comfort

7.4

Boarding

7.7

Entertainment

6.9

Overall

7.6

Crew

8.2

Food

6.7

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Tallinn. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Tallinn from Chicago?

    If you book a flight to Tallinn from Chicago, you will be flying to Tallinn, which is the city’s only airport. Tallinn (TLL) is located 2.1 mi from the center of Tallinn. There are 0 flights from Chicago to Tallinn per day from 4 different airlines.

  • How long is the flight from Chicago to Tallinn?

    Departing from Chicago to Tallinn will take you 31h. There are 4456 mi between Chicago and Tallinn.

  • What are the cheapest airlines flying from Chicago to Tallinn round-trip?

    Flying on Scandinavian Airlines is currently your cheapest option to Tallinn, with prices starting at $433. Additional round-trip tickets that might be worth considering are offered by United Airlines and Lufthansa, with the lowest prices starting at $486 and $539, respectively. Scandinavian Airlines is priced at 38% lower than the current average price of a flight leaving 3 months from now.

  • Can I find deals for flights from Chicago to Tallinn that include hotel bookings?

    Yes. In addition to deals on Chicago to Tallinn flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Tallinn?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Tallinn.

  • Can I find deals for business class flights from Chicago to Tallinn?

    Yes. Cheapflights offers flight deals from Chicago to Tallinn by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Tallinn?

    Currently, April is the cheapest month in which you can book a flight from Chicago to Tallinn (average of $431). Flying from Chicago to Tallinn in July is currently the most expensive (average of $808). 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.

See more FAQs

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Alternative routes for Chicago to Tallinn

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Tallinn flights
St. Louis to Tallinn flights
O'Hare Intl to Tartu flights

Top 4 airlines flying from Chicago to Tallinn

Discover the top 4 airlines that operate flights from Chicago to Tallinn. 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 January 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$433Average$523FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$486Average$680FlexibilityNo cancel feeOn-time69%
LufthansaCheapest$539Average$848FlexibilityNo cancel feeOn-time76%
FinnairCheapest$678Average$1,024FlexibilityNo cancel feeOn-time76%

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