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$444+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
TLL — CHI
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheapflights Tip: The best prices from Tallinn to Chicago are usually found in February or April, booked 85 days in advance, depart on a Thursday or Wednesday and return on a Monday

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 August 20, 2025.

Round-trip from

$444
(oojo)

Popular in

December

Cheapest in

February

Average price

$703
From Tallinn to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 20, 2025.

This oojo deal was found by Cheapflights users on 8/18. 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 11/57:00 amTLL - ORD
2 stops17h 45mScandinavian Airlines
Wed 11/197:20 pmORD - TLL
1 stop11h 50mScandinavian Airlines
Deal found 8/18$444
This oojo deal was found by Cheapflights users on 8/19. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/134:20 pmTLL - ORD
2 stops32h 25mScandinavian Airlines
Fri 12/267:20 pmORD - TLL
1 stop11h 50mScandinavian Airlines
Deal found 8/19$475
This Booking.com deal was found by Cheapflights users on 8/17. 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 10/26:00 amTLL - ORD
1 stop17h 55mSWISS
Thu 10/97:05 pmORD - TLL
1 stop22h 30mSWISS
Deal found 8/17$625
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Thu 10/22:40 pmTLL - ORD
2 stops35h 52mUnited Airlines
Thu 10/910:30 pmORD - TLL
1 stop17h 45mUnited Airlines
Deal found 8/17$651

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 August 20, 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

Wed 11/5

7:00 am-4:45 pm

2 stops17h 45m

Chicago O'Hare Intl

Wed 11/19

7:20 pm-3:10 pm

1 stop11h 50m

$444

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sat 12/13

4:20 pm-4:45 pm

2 stops32h 25m

Chicago O'Hare Intl

Fri 12/26

7:20 pm-3:10 pm

1 stop11h 50m

$475

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sun 11/30

3:10 pm-7:13 am

3 stops48h 03m

$489

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 10/9

5:00 pm-3:39 pm

3 stops54h 39m

$516

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Thu 10/9

7:35 pm-9:40 am

1 stop22h 05m

$525

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sun 11/30

6:55 pm-6:25 pm

1 stop31h 30m

$525

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

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 August 8, 2025.

To ensure you get the cheapest price possible for a flight from Tallinn to Chicago, you should look to book at least 85 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, August is the cheapest month in which you can book a flight from Tallinn to Chicago (average of $245). Flying from Tallinn to Chicago in March is currently the most expensive (average of $321). 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.

What is the cheapest time of day to fly from TLL to CHI?

Find hourly flight availability from Tallinn to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 20, 2025.

One of the essential ways to save on airfare from Tallinn to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 27% on airfare.

How much does it cost to fly round-trip from Tallinn to Chicago?

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 August 20, 2025.
Read reviews from past customers who have flown LOT and 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.
LOT
7.6
Good
1,110 reviews

Food

7.2

Boarding

7.6

Crew

8.2

Comfort

7.5

Entertainment

7.0

Overall

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2024

WAW - LAX

It was a small jet plane and they spoke very fast, difficult to understand flight departure instructions in English.
LOT
7.6
Good
1,110 reviews
LOT
7.6
Good
1,110 reviews

Food

7.2

Boarding

7.6

Crew

8.2

Comfort

7.5

Entertainment

7.0

Overall

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2024

WAW - LAX

It was a small jet plane and they spoke very fast, difficult to understand flight departure instructions in English.
Finnair
7.6
Good
1,320 reviews
LOT
7.6
Good
1,110 reviews

Food

7.2

Boarding

7.6

Crew

8.2

Comfort

7.5

Entertainment

7.0

Overall

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2024

WAW - LAX

It was a small jet plane and they spoke very fast, difficult to understand flight departure instructions in English.

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 fly from Tallinn to Chicago in about 17h 45m. 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, August is the cheapest month in which you can book a flight from Tallinn to Chicago (average of $245). Flying from Tallinn to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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