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$347+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
TLL — CHI
Apr 14 — Apr 211
Tue 4/14
Tue 4/21
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 March 15, 2026.

This Mytrip deal was found by Cheapflights users on 3/10. 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.
Thu 4/232:45 pm
TLL
-
ORD
2 stops35h 30m
Multiple Airlines
Mon 4/277:25 pm
ORD
-
TLL
2 stops13h 55m
Multiple Airlines
Deal found 3/10$488
This Booking.com deal was found by Cheapflights users on 3/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:45 am
TLL
-
ORD
1 stop22h 05m
LOT
Thu 6/49:50 pm
ORD
-
TLL
1 stop31h 50m
LOT
Deal found 3/14$493
This Booking.com deal was found by Cheapflights users on 3/10. 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 4/237:55 am
TLL
-
ORD
1 stop17h 55m
Finnair
Mon 4/279:30 pm
ORD
-
TLL
1 stop15h 25m
Finnair
Deal found 3/10$522
This Finnair deal was found by Cheapflights users on 3/11. 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 3/11$524
This Iberia deal was found by Cheapflights users on 3/15. 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 3/15$542
This Gotogate deal was found by Cheapflights users on 3/12. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:55 am
TLL
-
ORD
1 stop17h 55m
Finnair
Thu 6/49:30 pm
ORD
-
TLL
1 stop15h 25m
Finnair
Deal found 3/12$562

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 March 15, 2026.

Round-trip from

$488
(Mytrip)

One-way from

$347
(Kiwi.com)

Popular in

July

Cheapest in

April

Average price

$570
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 ($144 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 March 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 March 15, 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

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 4/23

6:00 am-5:50 pm

1 stop19h 50m

Chicago O'Hare Intl

Mon 4/27

9:30 pm-4:15 pm

1 stop10h 45m

$583

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 4/23

6:00 am-5:50 pm

1 stop19h 50m

Chicago O'Hare Intl

Mon 4/27

9:15 pm-10:50 pm

2 stops17h 35m

$583

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Tue 5/26

6:10 am-10:58 pm

2 stops24h 48m

Chicago O'Hare Intl

Mon 6/1

3:10 pm-1:05 pm

1 stop13h 55m

$789
Quickest round-trip

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sun 5/24

6:15 am-4:10 pm

1 stop17h 55m

Chicago O'Hare Intl

Fri 6/5

7:15 pm-3:15 pm

1 stop12h 00m

$791

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 5/27

6:00 am-3:00 pm

2 stops17h 00m

Chicago O'Hare Intl

Wed 6/3

4:29 pm-3:45 pm

2 stops15h 16m

$800

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sun 5/24

10:10 am-9:12 pm

2 stops19h 02m

Chicago O'Hare Intl

Mon 6/1

9:15 pm-11:35 pm

1 stop18h 20m

$804

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sat 5/23

10:10 am-7:33 pm

2 stops17h 23m

Chicago O'Hare Intl

Mon 6/1

9:15 pm-11:35 pm

1 stop18h 20m

$804

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sat 5/23

5:20 pm-5:50 pm

1 stop32h 30m

Chicago O'Hare Intl

Wed 6/3

4:29 pm-3:45 pm

2 stops15h 16m

$818

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 4/23

6:25 pm-4:00 pm

3 stops29h 35m

Chicago O'Hare Intl

Mon 4/27

9:50 am-7:55 pm

2 stops26h 05m

$1,128
Cheapest one-way

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Fri 4/17

5:35 pm-9:15 pm

2 stops35h 40m

$445

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/11

Showing 1-10 of 18 resultsSorted by cheapest first
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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 March 13, 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 $675). 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.

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 fly from Tallinn to Chicago in about 17h 55m. The time it takes to get you to your destination can typically vary by up to . The distance from Tallinn to Chicago is about 4456 mi.

  • 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 $675). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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