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$357+ 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 9 — Mar 161
Mon 3/9
Mon 3/16
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 7, 2026.

This Finnair deal was found by Cheapflights users on 2/4. 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 10/77:25 am
TLL
-
ORD
1 stop18h 25m
Finnair
Tue 10/139:30 pm
ORD
-
TLL
1 stop15h 25m
Finnair
Deal found 2/4$547
This Finnair deal was found by Cheapflights users on 2/6. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2310:20 pm
TLL
-
ORD
2 stops29h 20m
Finnair
Thu 3/54:10 pm
ORD
-
TLL
2 stops16h 25m
Finnair
Deal found 2/6$557
This American Airlines deal was found by Cheapflights users on 2/4. 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.
Tue 2/246:00 am
TLL
-
ORD
2 stops21h 40m
American Airlines
Thu 12/1012:02 pm
ORD
-
TLL
2 stops20h 03m
American Airlines
Deal found 2/4$572
This oojo deal was found by Cheapflights users on 2/4. 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.
Tue 2/248:00 pm
TLL
-
ORD
2 stops28h 45m
Scandinavian Airlines
Thu 12/107:20 pm
ORD
-
TLL
1 stop31h 10m
Scandinavian Airlines
Deal found 2/4$591
This Turkish Airlines deal was found by Cheapflights users on 2/5. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/511:25 am
TLL
-
ORD
1 stop39h 00m
Turkish Airlines
Sun 3/89:20 pm
ORD
-
TLL
1 stop37h 40m
Turkish Airlines
Deal found 2/5$595
This FlightHub deal was found by Cheapflights users on 2/4. 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.
Wed 2/253:40 pm
TLL
-
ORD
2 stops33h 05m
Scandinavian Airlines
Thu 12/107:20 pm
ORD
-
TLL
1 stop31h 10m
Scandinavian Airlines
Deal found 2/4$598
This American Airlines deal was found by Cheapflights users on 2/4. 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 10/710:55 am
TLL
-
ORD
2 stops18h 20m
Multiple Airlines
Tue 10/1312:03 pm
ORD
-
TLL
2 stops16h 22m
Multiple Airlines
Deal found 2/4$599

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 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$557
(Finnair)

One-way from

$357
(Finnair)

Popular in

July

Cheapest in

March

Average price

$457
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. 18% potential increase in price ($140 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 7, 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

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

$595

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Mon 2/23

10:20 pm-7:40 pm

2 stops29h 20m

Chicago O'Hare Intl

Sat 3/7

6:30 pm-10:00 pm

2 stops19h 30m

$619

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Tue 2/24

3:40 pm-4:45 pm

2 stops33h 05m

Chicago O'Hare Intl

Tue 12/8

7:20 pm-10:30 am

1 stop31h 10m

$626

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 3/5

8:00 pm-4:55 pm

2 stops28h 55m

Chicago O'Hare Intl

Sun 3/15

8:20 pm-10:20 am

1 stop31h 00m

$627

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 2/19

9:30 pm-5:00 pm

2 stops27h 30m

Chicago O'Hare Intl

Thu 3/5

4:10 pm-4:55 pm

2 stops16h 45m

$628

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Tue 2/24

3:40 pm-4:45 pm

2 stops33h 05m

Chicago O'Hare Intl

Sat 12/12

7:20 pm-11:40 pm

2 stops20h 20m

$634

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Tue 2/24

3:40 pm-4:45 pm

2 stops33h 05m

Chicago O'Hare Intl

Sun 12/13

7:20 pm-10:30 am

2 stops31h 10m

$634

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 2/25

11:00 am-4:45 pm

1 stop13h 45m

Chicago O'Hare Intl

Mon 12/7

7:20 pm-10:30 am

1 stop31h 10m

$636

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 2/19

8:00 pm-4:45 pm

2 stops28h 45m

Chicago O'Hare Intl

Thu 3/5

7:20 pm-10:20 am

1 stop31h 00m

$643

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sat 5/30

6:00 am-7:28 pm

2 stops21h 28m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 12 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 6, 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 $383). 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 Turkish Airlines and Finnair fly from Tallinn to Chicago in about 29h 20m. The time it takes to get you to your destination can typically vary by up to 9h 40m. 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 $383). 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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Hammond
Porter
Benton Harbor

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