HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Tallinn

$279+ Cheap flights from Chicago (CHI) to Tallinn (TLL)

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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TLL
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Tallinn with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Tallinn

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Tallinn (TLL). 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 October 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$433
(oojo)

One-way from

$279
(Kiwi.com)

Popular in

September

Cheapest in

March

Average price

$646
Provider with most accurate pricing for Chicago (CHI)-Tallinn flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Tallinn flights.
Search Deals
From Chicago (CHI) to Tallinn
Search Deals
One-way flight from Chicago (CHI) to Tallinn
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find flight deals from Chicago to Tallinn

Cheapest flights from Chicago to Tallinn
Explore the most affordable flight options available from Chicago to Tallinn. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 2, 2025.

This oojo deal was found by Cheapflights users on 10/1. 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 11/57:20 pmORD - TLL
1 stop11h 50mScandinavian Airlines
Sun 11/911:00 amTLL - ORD
1 stop13h 45mScandinavian Airlines
Deal found 10/1$433
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2911:35 pmORD - TLL
1 stop17h 15mLufthansa
Wed 11/51:55 pmTLL - ORD
1 stop14h 10mLufthansa
Deal found 10/1$444
This Mytrip deal was found by Cheapflights users on 10/1. 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.
Wed 10/297:50 pmORD - TLL
1 stop22h 15mMultiple Airlines
Wed 11/56:40 amTLL - ORD
2 stops16h 15mMultiple Airlines
Deal found 10/1$457
This United Airlines deal was found by Cheapflights users on 10/1. 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 10/292:10 pmORD - TLL
2 stops26h 40mUnited Airlines
Wed 11/56:00 amTLL - ORD
2 stops22h 00mUnited Airlines
Deal found 10/1$492
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/123:35 pmORD - TLL
1 stop18h 50mLufthansa
Mon 10/207:10 pmTLL - ORD
1 stop25h 20mLufthansa
Deal found 10/1$522
This United Airlines deal was found by Cheapflights users on 9/29. 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 12/246:25 pmORD - TLL
1 stop21h 25mUnited Airlines
Tue 1/66:05 pmTLL - ORD
2 stops34h 08mUnited Airlines
Deal found 9/29$548
This Mytrip deal was found by Cheapflights users on 10/1. 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.
Sun 10/1210:40 amORD - TLL
2 stops18h 25mMultiple Airlines
Mon 10/206:55 pmTLL - ORD
2 stops26h 25mMultiple Airlines
Deal found 10/1$580
This United Airlines deal was found by Cheapflights users on 9/29. 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 12/246:25 pmORD - TLL
1 stop21h 25mUnited Airlines
Wed 12/311:55 pmTLL - ORD
2 stops38h 05mUnited Airlines
Deal found 9/29$601
This Mytrip deal was found by Cheapflights users on 10/1. 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.
Wed 11/53:35 pmORD - TLL
3 stops18h 40mMultiple Airlines
Sun 11/96:50 amTLL - ORD
2 stops21h 15mMultiple Airlines
Deal found 10/1$616

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Tallinn 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 October 2, 2025.
Use the filters below to find and compare flights from Chicago to Tallinn that are best for you.

Fly from

Chicago

Fly to

Tallinn

Route

Depart

Return

Price

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Wed 11/5

7:20 pm-7:30 pm

2 stops16h 10m

Tallinn

Sun 11/9

11:00 am-4:45 pm

1 stop13h 45m

$433

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Wed 10/29

11:35 pm-11:50 pm

1 stop17h 15m

Tallinn

Wed 11/5

1:55 pm-8:05 pm

1 stop14h 10m

$444

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Wed 3/4

7:20 pm-1:25 am

1 stop22h 05m

Tallinn

Sun 3/8

11:00 am-5:45 pm

1 stop13h 45m

$458

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/1

Compare providers for flights from Chicago to Tallinn

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 Chicago to Tallinn in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 Chicago-Tallinn flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Tallinn flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Tallinn flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Tallinn flights, Cheapflights users trust FlightHub the most. FlightHub 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 Chicago-Tallinn 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 Chicago to Tallinn

Have a flexible travel schedule? Discover the best time to fly to Tallinn from Chicago 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 Chicago to Tallinn

What is the cheapest month to book a flight from Chicago to Tallinn?

Currently, November is the cheapest month in which you can book a flight from Chicago to Tallinn (average of $550). Flying from Chicago to Tallinn in June is currently the most expensive (average of $975). 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 CHI to TLL?

Find hourly flight availability from Chicago to Tallinn. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 2, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 21% on flights from Chicago to Tallinn by exploring options for tickets in the morning.

Reviews of airlines servicing Tallinn

Get insights into the airlines that provide service to Tallinn. 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 Tallinn. Reviews last updated October 2, 2025.
Read through reviews of airlines operating flights from Chicago to Tallinn, such as Finnair, Scandinavian Airlines, and Lufthansa. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Finnair
7.6
Good
1,332 reviews

Overall

7.6

Boarding

7.6

Entertainment

6.9

Crew

8.1

Food

6.7

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Daniel,May 2025

HEL - ARN

This is a very short flight. The crew was all very friendly and helpful. The plane was clean and nice. By the time you're in the air, you're starting to descend. It's painless.
Finnair
7.6
Good
1,332 reviews
Finnair
7.6
Good
1,332 reviews

Overall

7.6

Boarding

7.6

Entertainment

6.9

Crew

8.1

Food

6.7

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Daniel,May 2025

HEL - ARN

This is a very short flight. The crew was all very friendly and helpful. The plane was clean and nice. By the time you're in the air, you're starting to descend. It's painless.
Scandinavian Airlines
7.4
Good
1,514 reviews
Finnair
7.6
Good
1,332 reviews

Overall

7.6

Boarding

7.6

Entertainment

6.9

Crew

8.1

Food

6.7

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Daniel,May 2025

HEL - ARN

This is a very short flight. The crew was all very friendly and helpful. The plane was clean and nice. By the time you're in the air, you're starting to descend. It's painless.
Lufthansa
6.8
Okay
7,446 reviews
Finnair
7.6
Good
1,332 reviews

Overall

7.6

Boarding

7.6

Entertainment

6.9

Crew

8.1

Food

6.7

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Daniel,May 2025

HEL - ARN

This is a very short flight. The crew was all very friendly and helpful. The plane was clean and nice. By the time you're in the air, you're starting to descend. It's painless.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Tallinn. 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 into for flights to Tallinn from Chicago?

    If you book a flight to Tallinn from Chicago, you will be flying to Tallinn, which is the city’s only airport. Tallinn (TLL) is located 2.1 mi from the center of Tallinn. There are 0 flights from Chicago to Tallinn per day from 4 different airlines.

  • How long is the flight from Chicago to Tallinn?

    Departing from Chicago to Tallinn will take you 16h 10m. There are 4456 mi between Chicago and Tallinn. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Flying on Scandinavian Airlines is currently your cheapest option to Tallinn, with prices starting at $424. Additional round-trip tickets that might be worth considering are offered by Finnair and United Airlines, with the lowest prices starting at $513 and $529, respectively. Scandinavian Airlines is priced at 39% lower than the current average price of a flight leaving 3 months from now.

  • Can I find deals for flights from Chicago to Tallinn that include hotel bookings?

    Yes. In addition to deals on Chicago to Tallinn flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Tallinn?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Tallinn.

  • Can I find deals for business class flights from Chicago to Tallinn?

    Yes. Cheapflights offers flight deals from Chicago to Tallinn 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 Chicago to Tallinn?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Tallinn (average of $550). Flying from Chicago to Tallinn in June is currently the most expensive (average of $975). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Tallinn

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

Top 4 airlines flying from Chicago to Tallinn

Discover the top 4 airlines that operate flights from Chicago to Tallinn. 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 October 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$424Average$460FlexibilityNo cancel feeOn-time77%
FinnairCheapest$513Average$763FlexibilityNo cancel feeOn-time76%
United AirlinesCheapest$529Average$680FlexibilityNo cancel feeOn-time69%
LufthansaCheapest$535Average$725FlexibilityNo cancel feeOn-time76%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.