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$508+ Cheap flights from Tallinn (TLL) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
TLL — CHI
Dez 21 — Dez 281
So 12/21
So 12/28
1 adult, Economy
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Cheapflights Tip: The best prices from Tallinn to Chicago are usually found in February or April, booked 37 days in advance, depart on a Thursday or Wednesday and return on a Monday

Find 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 November 21, 2025.

This United Airlines deal was found by Cheapflights users on 11/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 12/286:15 amTLL - ORD
2 stops37h 03mUnited Airlines
Sa 1/39:15 pmORD - TLL
2 stops35h 55mUnited Airlines
Deal found 11/19$949
This Orbitz deal was found by Cheapflights users on 11/19. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 12/286:15 amTLL - ORD
1 stop14h 55mLufthansa
Sa 1/39:50 pmORD - TLL
2 stops31h 05mLufthansa
Deal found 11/19$980
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 12/286:50 amTLL - ORD
2 stops19h 05mMultiple Airlines
Sa 1/39:50 pmORD - TLL
3 stops26h 25mMultiple Airlines
Deal found 11/19$1,260

Cheap 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 November 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$508
(Mytrip)

Popular in

December

Cheapest in

February

Average price

$518
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
Highest demand for flights based on searches. 6% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 21, 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

Fr 2/20

3:45 pm-4:45 pm

1 stop33h 00m

Chicago O'Hare Intl

Fr 2/27

7:20 pm-10:20 am

1 stop31h 00m

$508

TallinnChicago

TLL - ORD

TLLORD

Tallinn

So 1/11

4:10 pm-4:45 pm

2 stops32h 35m

Chicago O'Hare Intl

Do 1/15

7:20 pm-10:20 am

1 stop31h 00m

$540

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Fr 3/13

11:25 am-7:25 pm

1 stop39h 00m

Chicago O'Hare Intl

Di 3/17

9:20 pm-6:00 pm

1 stop37h 40m

$693

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Fr 3/13

1:35 pm-9:05 pm

1 stop14h 30m

Chicago O'Hare Intl

Di 3/17

1:09 pm-1:10 pm

2 stops17h 01m

$713

TallinnChicago

TLL - ORD

TLLORD

Tallinn

So 1/11

3:40 pm-7:15 pm

3 stops35h 35m

Chicago O'Hare Intl

Do 1/15

7:20 pm-11:40 pm

2 stops20h 20m

$932

TallinnChicago

TLL - ORD

TLLORD

Tallinn

So 12/28

6:15 am-11:18 am

2 stops37h 03m

Chicago O'Hare Intl

Sa 1/3

9:15 pm-5:10 pm

2 stops35h 55m

$949

TallinnChicago

TLL - ORD

TLLORD

Tallinn

So 12/28

6:15 am-1:10 pm

1 stop14h 55m

Chicago O'Hare Intl

Sa 1/3

9:50 pm-12:55 pm

2 stops31h 05m

$980

TallinnChicago

TLL - ORD

TLLORD

Tallinn

So 1/25

2:05 pm-8:00 pm

1 stop13h 55m

$600

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Mo 1/26

11:00 am-4:45 pm

1 stop13h 45m

$2,131

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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 November.
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 November 14, 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 $329). 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 November 21, 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
1,334 reviews

Entertainment

6.9

Food

6.7

Overall

7.6

Crew

8.1

Comfort

7.4

Boarding

7.6

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
1,334 reviews
Finnair
7.6
Good
1,334 reviews

Entertainment

6.9

Food

6.7

Overall

7.6

Crew

8.1

Comfort

7.4

Boarding

7.6

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 Scandinavian Airlines and Turkish Airlines fly from Tallinn to Chicago in about 33h. The time it takes to get you to your destination can typically vary by up to 6h. 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 $329). 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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