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Estonia

$278+ Cheap flights from Chicago (CHI) to Estonia

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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TLL
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Chicago to Estonia

Keep the following information in mind while searching for Chicago to Estonia flight deals. Data was last updated August 20, 2025.

Round-trip from

$435
(oojo)

One-way from

$278
(Kiwi.com)

Popular in

June

Cheapest in

March

Average price

$710
From Chicago (CHI) to Estonia
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One-way flight from Chicago (CHI) to Estonia
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Highest demand for flights based on searches. 18% potential increase in price ($152 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 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 Chicago to Estonia

Cheapest flights from Chicago to Estonia
Explore the most affordable flight options available from Chicago to Estonia. 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 8/19. 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.
Mon 10/67:15 pmORD - TLL
2 stops12h 40mScandinavian Airlines
Wed 10/228:00 pmTLL - ORD
2 stops28h 10mScandinavian Airlines
Deal found 8/19$435
This Scandinavian Airlines 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:20 pmORD - TLL
1 stop11h 50mScandinavian Airlines
Fri 12/267:00 amTLL - ORD
2 stops41h 45mScandinavian Airlines
Deal found 8/18$437
This Scandinavian Airlines 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:20 pmORD - TLL
2 stops20h 20mScandinavian Airlines
Sat 12/274:20 pmTLL - ORD
2 stops32h 25mScandinavian Airlines
Deal found 8/18$444
This oojo deal was found by Cheapflights users on 8/20. 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.
Thu 11/207:20 pmORD - TLL
1 stop11h 50mScandinavian Airlines
Sun 12/74:10 pmTLL - ORD
2 stops32h 35mScandinavian Airlines
Deal found 8/20$495
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/410:55 amORD - TLL
2 stops18h 15mUnited Airlines
Wed 11/196:00 amTLL - ORD
1 stop15h 10mUnited Airlines
Deal found 8/19$502
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/412:50 pmORD - TLL
2 stops16h 00mMultiple Airlines
Wed 11/196:00 amTLL - ORD
2 stops21h 30mMultiple Airlines
Deal found 8/19$503
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/196:25 pmORD - TLL
1 stop15h 35mUnited Airlines
Tue 8/266:00 amTLL - ORD
1 stop13h 00mUnited Airlines
Deal found 8/19$550
This Finnair 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/65:40 pmORD - TLL
2 stops14h 30mFinnair
Wed 10/226:00 amTLL - ORD
2 stops19h 00mFinnair
Deal found 8/19$557
This Trip.com deal was found by Cheapflights users on 8/20. 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.
Sat 10/410:35 pmORD - TAY
2 stops18h 10mFinnair
Sat 10/116:00 amTAY - ORD
2 stops37h 50mFinnair
Deal found 8/20$740
This Mytrip deal was found by Cheapflights users on 8/20. 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.
Sat 10/43:45 pmORD - TAY
3 stops25h 00mMultiple Airlines
Sat 10/116:00 amTAY - ORD
3 stops21h 00mMultiple Airlines
Deal found 8/20$1,236

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Estonia 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 Chicago to Estonia that are best for you.

Fly from

Chicago

Fly to

Estonia

Route

Depart

Return

Price

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Mon 10/6

7:15 pm-3:10 pm

1 stop11h 55m

Tallinn

Wed 10/22

8:00 pm-4:10 pm

2 stops28h 10m

$435

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Wed 12/17

7:20 pm-3:10 pm

1 stop11h 50m

Tallinn

Thu 12/25

3:40 pm-4:45 pm

2 stops33h 05m

$437

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Wed 12/17

7:20 pm-3:10 pm

1 stop11h 50m

Tallinn

Fri 12/26

7:00 am-4:45 pm

2 stops41h 45m

$437

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Wed 12/17

7:20 pm-3:10 pm

1 stop11h 50m

Tallinn

Sat 12/27

4:20 pm-4:45 pm

2 stops32h 25m

$437

ChicagoTartu

ORD - TAY

ORDTAY

Chicago O'Hare Intl

Sat 10/4

10:35 pm-12:45 am

2 stops18h 10m

Tartu

Sat 10/11

6:00 am-11:50 am

2 stops37h 50m

$740

ChicagoTartu

ORD - TAY

ORDTAY

Chicago O'Hare Intl

Sat 10/4

3:45 pm-12:45 am

3 stops25h 00m

Tartu

Sat 10/11

6:00 am-7:00 pm

3 stops21h 00m

$1,236

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Sun 9/21

10:27 am-8:35 pm

2 stops26h 08m

$278

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Sun 9/21

11:25 am-11:40 am

1 stop16h 15m

$441

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Best time to book a flight from Chicago to Estonia

Have a flexible travel schedule? Discover the best time to fly to Estonia 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 Estonia

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

Currently, November is the cheapest month in which you can book a flight from Chicago to Estonia (average of $550). Flying from Chicago to Estonia in June is currently the most expensive (average of $971). 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 EE?

Find hourly flight availability from Chicago to Estonia. 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.

When flying from Chicago to Estonia, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Estonia

Get insights into the airlines that provide service to Estonia. 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 Estonia. Reviews last updated August 20, 2025.
Read through reviews of airlines operating flights from Chicago to Estonia, such as Finnair, Scandinavian Airlines, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Finnair
7.6
Good
1,320 reviews

Overall

7.6

Food

6.7

Boarding

7.6

Crew

8.1

Entertainment

6.9

Comfort

7.5

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
1,320 reviews
Finnair
7.6
Good
1,320 reviews

Overall

7.6

Food

6.7

Boarding

7.6

Crew

8.1

Entertainment

6.9

Comfort

7.5

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
1,471 reviews
Finnair
7.6
Good
1,320 reviews

Overall

7.6

Food

6.7

Boarding

7.6

Crew

8.1

Entertainment

6.9

Comfort

7.5

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.
United Airlines
7.4
Good
8,928 reviews
Finnair
7.6
Good
1,320 reviews

Overall

7.6

Food

6.7

Boarding

7.6

Crew

8.1

Entertainment

6.9

Comfort

7.5

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
7,337 reviews
Finnair
7.6
Good
1,320 reviews

Overall

7.6

Food

6.7

Boarding

7.6

Crew

8.1

Entertainment

6.9

Comfort

7.5

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 Estonia. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Estonia?

    Scandinavian Airlines and Finnair can get you from Chicago to Estonia in just under 11h 55m. Your travel time can differ by up to 6h 15m. There are 4456 mi between Chicago and Estonia. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Chicago to Estonia (average of $550). Flying from Chicago to Estonia in June is currently the most expensive (average of $971). 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

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Alternative routes for Chicago to Estonia

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chicago to Estonia

Discover the top 4 airlines that operate flights from Chicago to Estonia. 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$424Average$460FlexibilityNo cancel feeOn-time77%
FinnairCheapest$507Average$740FlexibilityNo cancel feeOn-time76%
United AirlinesCheapest$528Average$680FlexibilityNo cancel feeOn-time69%
LufthansaCheapest$535Average$625FlexibilityNo cancel feeOn-time76%

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