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$404+ 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 7/27. Fares are subject to change and may not be available on all flights or dates of travel.
TLL — CHI
Jul 7 — Jul 141
Tue 7/7
Tue 7/14
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 June 7, 2026.

This Iberia deal was found by Cheapflights users on 6/6. 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 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 6/6$492
This Iberia deal was found by Cheapflights users on 6/6. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/298:10 am
TLL
-
ORD
2 stops23h 20m
Multiple Airlines
Wed 9/99:30 pm
ORD
-
TLL
1 stop10h 15m
Multiple Airlines
Deal found 6/6$497
This Iberia deal was found by Cheapflights users on 6/6. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:55 am
TLL
-
ORD
2 stops17h 38m
Multiple Airlines
Tue 10/139:30 pm
ORD
-
TLL
1 stop10h 45m
Multiple Airlines
Deal found 6/6$498
This Iberia deal was found by Cheapflights users on 6/5. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/298:10 am
TLL
-
ORD
2 stops21h 06m
Iberia
Tue 9/19:30 pm
ORD
-
TLL
1 stop10h 15m
Iberia
Deal found 6/5$533
This Finnair deal was found by Cheapflights users on 6/5. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:00 am
TLL
-
ORD
2 stops18h 50m
Finnair
Tue 10/139:40 pm
ORD
-
TLL
2 stops15h 15m
Finnair
Deal found 6/5$541
This Finnair deal was found by Cheapflights users on 6/6. 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.
Wed 9/26:00 am
TLL
-
ORD
2 stops21h 42m
Finnair
Wed 9/94:01 pm
ORD
-
TLL
2 stops15h 44m
Finnair
Deal found 6/6$542

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 June 7, 2026.

Round-trip from

$492
(Iberia)

One-way from

$404
(Travelocity)

Popular in

June

Cheapest in

April

Average price

$894
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 ($160 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 7, 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

Wed 10/7

6:00 am-4:50 pm

2 stops18h 50m

Chicago O'Hare Intl

Tue 10/13

9:40 pm-10:50 pm

2 stops17h 10m

$541

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 9/2

6:00 am-7:42 pm

2 stops21h 42m

Chicago O'Hare Intl

Wed 9/9

4:01 pm-3:45 pm

2 stops15h 44m

$542

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sat 8/29

9:20 pm-5:35 pm

2 stops28h 15m

Chicago O'Hare Intl

Wed 9/9

12:09 pm-12:25 pm

2 stops16h 16m

$548

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sat 8/29

6:25 am-4:10 pm

2 stops17h 45m

Chicago O'Hare Intl

Tue 9/1

6:00 am-3:15 pm

2 stops25h 15m

$629
Quickest round-trip

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Fri 8/28

7:00 am-4:10 pm

2 stops17h 10m

Chicago O'Hare Intl

Thu 9/3

7:15 pm-3:15 pm

1 stop12h 00m

$641

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Fri 8/28

7:00 am-4:10 pm

2 stops17h 10m

Chicago O'Hare Intl

Tue 9/1

7:15 pm-3:15 pm

1 stop12h 00m

$641

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 7/1

11:15 pm-1:50 pm

2 stops22h 35m

Chicago O'Hare Intl

Tue 7/28

9:30 pm-12:50 am

1 stop19h 20m

$758

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 7/1

6:15 am-4:10 pm

1 stop17h 55m

Chicago O'Hare Intl

Tue 7/28

7:15 pm-3:15 pm

1 stop12h 00m

$801
Cheapest one-way

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Tue 7/28

6:00 am-12:30 pm

2 stops38h 30m

$470

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Mon 7/20

9:40 pm-4:00 pm

3 stops50h 20m

$548

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/2

Showing 1-10 of 18 resultsSorted by cheapest first
1
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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

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 $309). Flying from Tallinn to Chicago in July is currently the most expensive (average of $643). 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?

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 33 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 Finnair fly from Tallinn to Chicago in about 18h 50m. 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, April is the cheapest month in which you can book a flight from Tallinn to Chicago (average of $309). Flying from Tallinn to Chicago in July is currently the most expensive (average of $643). 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
Hammond
Porter

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