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$333+ Cheap flights from Tallinn (TLL) to Chicago (CHI)

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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
TLL — CHI
Mar 23 — Mar 301
Mon 3/23
Mon 3/30
1 adult, Economy
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Cheap flight deals from Tallinn to Chicago

Cheapest flights from Tallinn to Chicago
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 February 21, 2026.

This Iberia deal was found by Cheapflights users on 2/21. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/73:00 pm
TLL
-
ORD
1 stop10h 50m
Iberia
Tue 10/139:30 pm
ORD
-
TLL
1 stop10h 45m
Iberia
Deal found 2/21$551
This Finnair deal was found by Cheapflights users on 2/19. 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.
Sun 4/268:10 am
TLL
-
ORD
1 stop17h 40m
Finnair
Mon 5/119:30 pm
ORD
-
TLL
1 stop16h 45m
Finnair
Deal found 2/19$563
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Sun 4/266:00 am
TLL
-
ORD
1 stop19h 50m
American Airlines
Mon 5/113:57 pm
ORD
-
TLL
2 stops15h 48m
American Airlines
Deal found 2/19$568
This American Airlines deal was found by Cheapflights users on 2/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:00 am
TLL
-
ORD
2 stops21h 57m
American Airlines
Mon 5/119:30 pm
ORD
-
TLL
1 stop10h 15m
American Airlines
Deal found 2/18$574
This Finnair deal was found by Cheapflights users on 2/20. 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.
Wed 10/712:50 pm
TLL
-
ORD
1 stop13h 00m
Finnair
Tue 10/139:40 pm
ORD
-
TLL
2 stops15h 15m
Finnair
Deal found 2/20$577
This American Airlines deal was found by Cheapflights users on 2/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:15 pm
TLL
-
ORD
1 stop26h 35m
Multiple Airlines
Mon 5/119:30 pm
ORD
-
TLL
1 stop10h 15m
Multiple Airlines
Deal found 2/18$582
This American Airlines deal was found by Cheapflights users on 2/21. 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 10/76:00 am
TLL
-
ORD
1 stop19h 50m
Multiple Airlines
Tue 10/1312:03 pm
ORD
-
TLL
2 stops16h 22m
Multiple Airlines
Deal found 2/21$585

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 February 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$563
(Finnair)

One-way from

$333
(Finnair)

Popular in

July

Cheapest in

April

Average price

$472
Provider with most accurate pricing for Tallinn-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Tallinn-Chicago (CHI) flights.
Search Deals
From Tallinn to Chicago (CHI)
Search Deals
One-way flight from Tallinn to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($143 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 2,558,603 searches. Data last updated February 21, 2026.
Use the filters below to find and compare flights from Tallinn to Chicago that are best for you.

Fly from

Tallinn

Fly to

Chicago

Route

Depart

Return

Price

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sun 4/26

8:10 am-5:50 pm

1 stop17h 40m

Chicago O'Hare Intl

Mon 5/11

9:30 pm-10:15 pm

1 stop16h 45m

$563

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sun 4/26

6:00 am-5:50 pm

1 stop19h 50m

Chicago O'Hare Intl

Mon 5/11

3:57 pm-3:45 pm

2 stops15h 48m

$568

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 3/5

11:25 am-6:25 pm

1 stop39h 00m

Chicago O'Hare Intl

Sun 3/15

9:20 pm-6:00 pm

1 stop37h 40m

$593

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sun 4/26

10:10 am-7:57 pm

2 stops17h 47m

Chicago O'Hare Intl

Mon 5/11

3:57 pm-3:45 pm

2 stops15h 48m

$596

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 3/5

11:25 am-6:25 pm

1 stop39h 00m

Chicago O'Hare Intl

Sun 3/8

9:20 pm-6:00 pm

1 stop37h 40m

$597

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 3/5

8:25 am-7:40 pm

2 stops19h 15m

Chicago O'Hare Intl

Sun 3/15

1:14 pm-2:15 pm

2 stops18h 01m

$614

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 5/27

3:00 pm-5:50 pm

1 stop10h 50m

Chicago O'Hare Intl

Mon 6/1

7:25 pm-5:20 pm

2 stops13h 55m

$676

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 3/5

5:40 am-8:00 pm

1 stop22h 20m

Chicago O'Hare Intl

Sun 3/15

10:55 pm-1:45 am

2 stops19h 50m

$678

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Fri 7/10

11:15 am-9:40 am

1 stop30h 25m

Chicago O'Hare Intl

Fri 7/24

11:25 am-6:40 pm

1 stop23h 15m

$695

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 5/27

10:55 am-5:00 am

2 stops26h 05m

Chicago O'Hare Intl

Sun 5/31

11:40 am-12:25 pm

2 stops16h 45m

$700

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 13 results
1
2
  • Most accurate provider: When it comes to deals on Tallinn-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Tallinn-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Tallinn-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Tallinn-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub 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 Tallinn-Chicago 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 Tallinn to Chicago

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

How far ahead should I book a flight from Tallinn to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Tallinn to Chicago. Price data was last updated on February 18, 2026.

To ensure you get the cheapest price possible for a flight from Tallinn to Chicago, you should look to book at least 41 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.

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

Currently, March is the cheapest month in which you can book a flight from Tallinn to Chicago (average of $387). Flying from Tallinn to Chicago in June is currently the most expensive (average of $673). 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?

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.

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

    Located just 2.1 mi from the city center, Tallinn is the airport most travelers will use when flying to Chicago from Tallinn. Booking flights from Tallinn (TLL) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 0 different airlines.

  • How long is the flight from Tallinn to Chicago?

    Airlines like Finnair, American Airlines, and Turkish Airlines fly from Tallinn to Chicago in about 17h 40m. The time it takes to get you to your destination can typically vary by up to 21h 20m. The distance from Tallinn to Chicago is about 4456 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Tallinn to Chicago 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 Tallinn to Chicago?

    Currently, March is the cheapest month in which you can book a flight from Tallinn to Chicago (average of $387). Flying from Tallinn to Chicago in June is currently the most expensive (average of $673). 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

Traveling to a place near Chicago?

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Lansing
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Hammond
Porter
Benton Harbor

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