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$330+ 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
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Tallinn to Chicago are usually found in February or November, booked 37 days in advance, depart on a Thursday or Wednesday and return on a Monday

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 December 23, 2025.

This Finnair deal was found by Cheapflights users on 12/21. 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 12/245:00 pmTLL - ORD
2 stops30h 25mFinnair
Wed 12/316:30 pmORD - TLL
2 stops18h 35mFinnair
Deal found 12/21$824
This oojo deal was found by Cheapflights users on 12/21. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:30 pmTLL - ORD
1 stop33h 30mLOT
Wed 12/319:55 pmORD - TLL
1 stop19h 50mLOT
Deal found 12/21$925
This United Airlines deal was found by Cheapflights users on 12/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:55 pmTLL - ORD
1 stop14h 10mUnited Airlines
Wed 12/319:15 pmORD - TLL
2 stops31h 35mUnited Airlines
Deal found 12/21$970
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/246:00 amTLL - ORD
3 stops19h 00mMultiple Airlines
Wed 12/311:15 pmORD - TLL
2 stops18h 00mMultiple Airlines
Deal found 12/21$2,910

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 December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$499
(Justfly.com)

One-way from

$330
(Finnair)

Popular in

June

Cheapest in

February

Average price

$744
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. 9% potential increase in price ($68 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 23, 2025.
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 2/5

6:30 pm-8:00 pm

1 stop33h 30m

Chicago O'Hare Intl

Sat 2/14

9:55 pm-1:25 pm

1 stop31h 30m

$499

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 3/5

3:45 pm-4:55 pm

1 stop33h 10m

Chicago O'Hare Intl

Sun 3/15

8:20 pm-10:20 am

1 stop31h 00m

$551

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sat 2/14

4:20 pm-4:55 pm

2 stops32h 35m

Chicago O'Hare Intl

Wed 2/18

7:20 pm-3:10 pm

1 stop11h 50m

$568

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 2/5

6:25 am-4:45 pm

1 stop18h 20m

Chicago O'Hare Intl

Thu 2/12

7:20 pm-10:20 am

1 stop31h 00m

$569

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Tue 3/17

8:25 am-9:26 pm

2 stops20h 01m

Chicago O'Hare Intl

Tue 3/31

1:15 pm-12:25 pm

2 stops15h 10m

$572

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sat 5/30

8:10 am-7:33 pm

2 stops19h 23m

$330

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sat 5/30

6:00 am-5:50 pm

1 stop19h 50m

$366

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Compare providers for flights from Tallinn to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Tallinn to Chicago in December.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Tallinn-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Tallinn-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 December 19, 2025.

To ensure you get the cheapest price possible for a flight from Tallinn to Chicago, you should look to book at least 36 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, April is the cheapest month in which you can book a flight from Tallinn to Chicago (average of $332). Flying from Tallinn to Chicago in June is currently the most expensive (average of $654). 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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated December 23, 2025.
Read reviews from past customers who have flown Finnair from Tallinn to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Finnair
7.6
Good
1,339 reviews

Overall

7.6

Boarding

7.6

Comfort

7.4

Crew

8.1

Entertainment

6.9

Food

6.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

FRA - DFW

I was lucky I had a seet without no one next to me My vegetarian meal was excellent. The service very good. Although there was a lot of turbulences during the flight, the landing was very soft and took away all our apprehension.
Finnair
7.6
Good
1,339 reviews
Finnair
7.6
Good
1,339 reviews

Overall

7.6

Boarding

7.6

Comfort

7.4

Crew

8.1

Entertainment

6.9

Food

6.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

FRA - DFW

I was lucky I had a seet without no one next to me My vegetarian meal was excellent. The service very good. Although there was a lot of turbulences during the flight, the landing was very soft and took away all our apprehension.

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 LOT and Scandinavian Airlines fly from Tallinn to Chicago in about 33h 10m. The time it takes to get you to your destination can typically vary by up to 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, April is the cheapest month in which you can book a flight from Tallinn to Chicago (average of $332). Flying from Tallinn to Chicago in June is currently the most expensive (average of $654). 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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