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$441+ 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
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$441
(oojo)

Popular in

July

Cheapest in

February

Average price

$750
From Tallinn to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($111 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 12, 2025.

This oojo deal was found by Cheapflights users on 6/12. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/58:00 pmTLL - ORD
2 stops28h 45mScandinavian Airlines
Wed 11/197:20 pmORD - TLL
1 stop11h 50mScandinavian Airlines
Deal found 6/12$441
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/16:00 amTLL - ORD
2 stops40h 38mUnited Airlines
Sat 8/97:30 amORD - TLL
2 stops26h 45mUnited Airlines
Deal found 6/11$686
This Trip.com deal was found by Cheapflights users on 6/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1812:35 pmTLL - ORD
1 stop29h 05mTurkish Airlines
Sat 7/267:50 pmORD - TLL
1 stop31h 50mTurkish Airlines
Deal found 6/11$767
This KLM deal was found by Cheapflights users on 6/11. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/17:30 amTLL - ORD
1 stop14h 40mKLM
Sat 8/94:20 pmORD - TLL
1 stop12h 55mKLM
Deal found 6/11$868
This Orbitz deal was found by Cheapflights users on 6/11. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/186:00 amTLL - ORD
1 stop14h 10mMultiple Airlines
Sat 7/269:40 pmORD - TLL
2 stops18h 40mMultiple Airlines
Deal found 6/11$870

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 12, 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

8:00 pm-4:45 pm

2 stops28h 45m

Chicago O'Hare Intl

Wed 11/19

7:20 pm-3:10 pm

1 stop11h 50m

$441

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Fri 8/1

6:00 am-2:38 pm

2 stops40h 38m

Chicago O'Hare Intl

Sat 8/9

7:30 am-6:15 pm

2 stops26h 45m

$686

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Fri 7/18

12:35 pm-9:40 am

1 stop29h 05m

Chicago O'Hare Intl

Sat 7/26

7:50 pm-11:40 am

1 stop31h 50m

$767

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Fri 8/1

7:30 am-2:10 pm

1 stop14h 40m

Chicago O'Hare Intl

Sat 8/9

4:20 pm-1:15 pm

1 stop12h 55m

$868

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Fri 7/18

6:00 am-12:10 pm

1 stop14h 10m

Chicago O'Hare Intl

Sat 7/26

9:40 pm-12:20 am

2 stops18h 40m

$870

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sat 8/30

5:45 am-7:40 pm

1 stop21h 55m

$497

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sat 8/30

6:25 am-4:15 pm

2 stops41h 50m

$576

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Sun 8/3

12:35 pm-9:40 am

1 stop29h 05m

$599

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 June 9, 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 June 12, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
KLM
7.8
Good
1,358 reviews

Boarding

7.8

Comfort

7.7

Entertainment

7.1

Overall

7.8

Food

7.2

Crew

8.4

Reviews

1 / 20
8.0
Excellent

Allan,Jun 2025

YYZ - AMS

I always enjoy flying KLM. Service is attentive, friendly and professional. The seat, when fully reclined is a little hard; some kind of mattress or topper would be helpful here. The dinner was really not very good …. “Meatless meatballs” tasted quite peculiar. Breakfast which consisted of an egg white omelette in flour tortilla was also rather tasteless.
KLM
7.8
Good
1,358 reviews
KLM
7.8
Good
1,358 reviews

Boarding

7.8

Comfort

7.7

Entertainment

7.1

Overall

7.8

Food

7.2

Crew

8.4

Reviews

1 / 20
8.0
Excellent

Allan,Jun 2025

YYZ - AMS

I always enjoy flying KLM. Service is attentive, friendly and professional. The seat, when fully reclined is a little hard; some kind of mattress or topper would be helpful here. The dinner was really not very good …. “Meatless meatballs” tasted quite peculiar. Breakfast which consisted of an egg white omelette in flour tortilla was also rather tasteless.
LOT
7.6
Good
1,077 reviews
KLM
7.8
Good
1,358 reviews

Boarding

7.8

Comfort

7.7

Entertainment

7.1

Overall

7.8

Food

7.2

Crew

8.4

Reviews

1 / 20
8.0
Excellent

Allan,Jun 2025

YYZ - AMS

I always enjoy flying KLM. Service is attentive, friendly and professional. The seat, when fully reclined is a little hard; some kind of mattress or topper would be helpful here. The dinner was really not very good …. “Meatless meatballs” tasted quite peculiar. Breakfast which consisted of an egg white omelette in flour tortilla was also rather tasteless.
United Airlines
7.4
Good
8,790 reviews
KLM
7.8
Good
1,358 reviews

Boarding

7.8

Comfort

7.7

Entertainment

7.1

Overall

7.8

Food

7.2

Crew

8.4

Reviews

1 / 20
8.0
Excellent

Allan,Jun 2025

YYZ - AMS

I always enjoy flying KLM. Service is attentive, friendly and professional. The seat, when fully reclined is a little hard; some kind of mattress or topper would be helpful here. The dinner was really not very good …. “Meatless meatballs” tasted quite peculiar. Breakfast which consisted of an egg white omelette in flour tortilla was also rather tasteless.
Turkish Airlines
7.3
Good
3,848 reviews
KLM
7.8
Good
1,358 reviews

Boarding

7.8

Comfort

7.7

Entertainment

7.1

Overall

7.8

Food

7.2

Crew

8.4

Reviews

1 / 20
8.0
Excellent

Allan,Jun 2025

YYZ - AMS

I always enjoy flying KLM. Service is attentive, friendly and professional. The seat, when fully reclined is a little hard; some kind of mattress or topper would be helpful here. The dinner was really not very good …. “Meatless meatballs” tasted quite peculiar. Breakfast which consisted of an egg white omelette in flour tortilla was also rather tasteless.
Scandinavian Airlines
7.3
Good
1,387 reviews
KLM
7.8
Good
1,358 reviews

Boarding

7.8

Comfort

7.7

Entertainment

7.1

Overall

7.8

Food

7.2

Crew

8.4

Reviews

1 / 20
8.0
Excellent

Allan,Jun 2025

YYZ - AMS

I always enjoy flying KLM. Service is attentive, friendly and professional. The seat, when fully reclined is a little hard; some kind of mattress or topper would be helpful here. The dinner was really not very good …. “Meatless meatballs” tasted quite peculiar. Breakfast which consisted of an egg white omelette in flour tortilla was also rather tasteless.

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 1 airline.

  • What are the cheapest airlines flying from Tallinn to Chicago round-trip?

    According to our current data, Scandinavian Airlines ($441), United Airlines ($686), and Turkish Airlines ($767) offers the cheapest pricing from Tallinn to Chicago. Users have found that Scandinavian Airlines is 29% cheaper than the other options available to this destination.

  • 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 Tallinn?

Book flights to Tallinn if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Tallinn to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Tallinn to O'Hare Intl flights

Top airline flying from Tallinn to Chicago

Discover the top airline that operate flights from Tallinn to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
LOTCheapest$547Average$612FlexibilityNo cancel feeOn-time81%

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