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$289+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
TLL — CHI
Aug 23 — Aug 301
Sun 8/23
Sun 8/30
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 July 24, 2026.

This Iberia deal was found by Cheapflights users on 7/24. 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.
Sat 9/58:10 am
TLL
-
ORD
1 stop17h 40m
Iberia
Wed 9/99:30 pm
ORD
-
TLL
1 stop10h 15m
Iberia
Deal found 7/24$490
This Finnair deal was found by Cheapflights users on 7/21. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:00 am
TLL
-
ORD
1 stop19h 50m
Finnair
Fri 9/118:50 pm
ORD
-
TLL
2 stops18h 00m
Finnair
Deal found 7/21$540
This oojo deal was found by Cheapflights users on 7/20. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:00 am
TLL
-
ORD
2 stops17h 10m
Scandinavian Airlines
Tue 10/137:15 pm
ORD
-
TLL
1 stop31h 30m
Scandinavian Airlines
Deal found 7/20$542
This British Airways deal was found by Cheapflights users on 7/22. 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 British Airways 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
British Airways
Tue 10/139:30 pm
ORD
-
TLL
1 stop17h 20m
British Airways
Deal found 7/22$543
This Finnair deal was found by Cheapflights users on 7/21. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:55 am
TLL
-
ORD
2 stops16h 41m
Finnair
Tue 10/139:05 pm
ORD
-
TLL
2 stops17h 45m
Finnair
Deal found 7/21$545
This Finnair deal was found by Cheapflights users on 7/19. 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.
Thu 8/279:20 pm
TLL
-
ORD
2 stops25h 40m
Finnair
Tue 9/19:15 pm
ORD
-
TLL
2 stops17h 35m
Finnair
Deal found 7/19$548
This Finnair deal was found by Cheapflights users on 7/24. 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.
Sat 9/58:10 am
TLL
-
ORD
2 stops19h 32m
Finnair
Wed 9/95:55 pm
ORD
-
TLL
2 stops15h 00m
Finnair
Deal found 7/24$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 July 24, 2026.

Round-trip from

$490
(Iberia)

One-way from

$289
(Booking.com)

Popular in

June

Cheapest in

April

Average price

$824
From Tallinn to Chicago (CHI)
Search Deals
One-way flight from Tallinn to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($162 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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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 July 24, 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

Price

Cheapest round-trip
Quickest round-trip

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sat 9/5

8:10 am-9:16 pm

2 stops21h 06m

Chicago O'Hare Intl

Wed 9/9

9:30 pm-3:45 pm

1 stop10h 15m

$496

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Fri 9/4

6:00 am-5:50 pm

1 stop19h 50m

Chicago O'Hare Intl

Fri 9/11

8:50 pm-10:50 pm

2 stops18h 00m

$540

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 10/7

6:00 am-5:50 pm

1 stop19h 50m

Chicago O'Hare Intl

Tue 10/13

9:30 pm-10:50 pm

1 stop17h 20m

$543

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 10/7

10:55 am-7:36 pm

2 stops16h 41m

Chicago O'Hare Intl

Tue 10/13

9:05 pm-10:50 pm

2 stops17h 45m

$544

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 8/27

9:20 pm-3:00 pm

2 stops25h 40m

Chicago O'Hare Intl

Tue 9/1

9:15 pm-10:50 pm

2 stops17h 35m

$548

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 8/27

6:00 am-5:50 pm

1 stop19h 50m

Chicago O'Hare Intl

Tue 9/1

9:30 pm-8:55 pm

1 stop15h 25m

$562

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Fri 8/21

6:00 am-3:00 pm

2 stops17h 00m

Chicago O'Hare Intl

Wed 8/26

9:45 pm-8:55 pm

2 stops15h 10m

$591

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sun 11/8

6:25 am-4:45 pm

1 stop18h 20m

Chicago O'Hare Intl

Wed 11/11

7:15 pm-10:30 am

1 stop31h 15m

$612
Cheapest one-way

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 9/24

7:55 am-5:50 pm

1 stop17h 55m

$289

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Tue 10/27

5:50 am-6:50 pm

1 stop20h 00m

$292

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

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

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 below average for this route at the moment.
Tallinn to Chicago flights typically cost between $648 and $862 in September.
The cheapest round-trip price found within the last 5 days was $490 on Iberia (Sep 5-Sep 9).

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 75 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.

  • 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 Iberia, Finnair, and British Airways fly from Tallinn to Chicago in about 19h 50m. The time it takes to get you to your destination can typically vary by up to 1h 16m. 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, 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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