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$257+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TLL
jun 23 — jun 301
seg 6/23
seg 6/30
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 junho 18, 2025.

Round-trip from

$448
(oojo)

One-way from

$257
(Kiwi.com)

Popular in

July

Cheapest in

March

Average price

$856
From Chicago (CHI) to Estonia
Search Deals
One-way flight from Chicago (CHI) to Estonia
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($197 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junho 18, 2025.

This oojo deal was found by Cheapflights users on 6/16. 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.
seg 8/47:15 pmORD - TLL
2 stops31h 10mScandinavian Airlines
seg 8/188:00 pmTLL - ORD
2 stops28h 10mScandinavian Airlines
Deal found 6/16$448
This Mytrip deal was found by Cheapflights users on 6/16. 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.
dom 8/107:05 pmORD - TLL
1 stop22h 30mMultiple Airlines
ter 8/267:20 amTLL - ORD
2 stops15h 35mMultiple Airlines
Deal found 6/16$485
This lol.travel deal was found by Cheapflights users on 6/16. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 8/107:05 pmORD - TLL
1 stop22h 30mSWISS
ter 8/266:00 amTLL - ORD
1 stop17h 55mSWISS
Deal found 6/16$492
This Mytrip deal was found by Cheapflights users on 6/16. 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.
dom 8/102:00 pmORD - TLL
2 stops15h 10mAir Canada
ter 8/267:20 amTLL - ORD
2 stops15h 35mAir Canada
Deal found 6/16$493
This United Airlines deal was found by Cheapflights users on 6/16. 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.
qua 9/33:05 pmORD - TLL
1 stop14h 50mUnited Airlines
qua 9/106:00 amTLL - ORD
2 stops35h 08mUnited Airlines
Deal found 6/16$536
This FlightHub deal was found by Cheapflights users on 6/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 9/310:30 pmORD - TLL
1 stop17h 50mLufthansa
qua 9/106:50 pmTLL - ORD
1 stop26h 05mLufthansa
Deal found 6/18$548
This Trip.com deal was found by Cheapflights users on 6/16. 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.
qua 8/611:45 pmORD - TLL
1 stop27h 55mTurkish Airlines
dom 8/1012:35 pmTLL - ORD
1 stop29h 05mTurkish Airlines
Deal found 6/16$927
This Ovago deal was found by Cheapflights users on 6/16. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 6/238:30 pmORD - TLL
2 stops17h 25mFinnair
qua 7/95:50 pmTLL - ORD
2 stops26h 05mFinnair
Deal found 6/16$948
This KLM deal was found by Cheapflights users on 6/17. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 7/254:20 pmORD - TLL
1 stop19h 35mKLM
qui 7/312:05 pmTLL - ORD
1 stop32h 05mKLM
Deal found 6/17$987
This Icelandair deal was found by Cheapflights users on 6/16. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 7/110:15 pmORD - TLL
1 stop25h 15mIcelandair
qua 8/611:25 pmTLL - ORD
1 stop29h 50mIcelandair
Deal found 6/16$1,048
This Trip.com deal was found by Cheapflights users on 6/16. 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.
qui 7/319:30 pmORD - TAY
1 stop10h 30mMultiple Airlines
qui 8/73:55 pmTAY - ORD
2 stops28h 00mMultiple Airlines
Deal found 6/16$1,240
This Booking.com deal was found by Cheapflights users on 6/17. 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.
sex 8/14:55 pmORD - TAY
2 stops37h 35mFinnair
sex 8/84:25 pmTAY - ORD
1 stop33h 00mFinnair
Deal found 6/17$1,358

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 junho 18, 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

seg 8/4

7:15 pm-10:25 am

2 stops31h 10m

Tallinn

seg 8/18

8:00 pm-4:10 pm

2 stops28h 10m

$448

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

dom 8/10

7:05 pm-1:35 am

1 stop22h 30m

Tallinn

ter 8/26

7:20 am-2:55 pm

2 stops15h 35m

$485

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

dom 8/10

7:05 pm-1:35 am

1 stop22h 30m

Tallinn

ter 8/26

6:00 am-3:55 pm

1 stop17h 55m

$492

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

dom 8/10

2:00 pm-1:10 pm

2 stops15h 10m

Tallinn

ter 8/26

7:20 am-2:55 pm

2 stops15h 35m

$493

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

qua 9/3

3:05 pm-1:55 pm

1 stop14h 50m

Tallinn

qua 9/10

6:00 am-9:08 am

2 stops35h 08m

$536

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

qua 9/3

10:30 pm-12:20 am

1 stop17h 50m

Tallinn

qua 9/10

6:50 pm-12:55 pm

1 stop26h 05m

$548

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

qua 8/6

11:45 pm-11:40 am

1 stop27h 55m

Tallinn

dom 8/10

12:35 pm-9:40 am

1 stop29h 05m

$927

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

sex 7/25

4:20 pm-7:55 pm

1 stop19h 35m

Tallinn

qui 7/31

2:05 pm-2:10 pm

1 stop32h 05m

$987

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

ter 7/1

10:15 pm-7:30 am

1 stop25h 15m

Tallinn

qua 8/6

11:25 pm-9:15 pm

1 stop29h 50m

$1,048

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

dom 6/29

8:30 pm-9:05 am

2 stops28h 35m

Tallinn

qui 8/7

10:00 am-11:59 pm

2 stops21h 59m

$1,078

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/18

Showing 1-10 of 19 results
1
2

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 $986). 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 junho 18, 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.

Rainfall in Estonia by month

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

In terms of precipitation, rainfall in Estonia ranges from 1.3 - 3.3 inches per month. August is typically the wettest month, when rainfall can reach 3.3 in. February is typically the driest time to visit Estonia when rainfall is around 1.3 in.

Temperature in Estonia by month

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

If weather is an important factor for your trip to Estonia, 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 62.6 F. Travelers looking to avoid the cold should look outside of February, when temperatures are typically at their lowest (around 23.0 F).

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 junho 18, 2025.
Get a feel of what it's like to fly with KLM, Finnair and SWISS from Chicago to Estonia by reading reviews from past customers. 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.
KLM
7.8
Good
1,363 reviews

Food

7.2

Overall

7.8

Comfort

7.7

Crew

8.4

Boarding

7.8

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.
KLM
7.8
Good
1,363 reviews
KLM
7.8
Good
1,363 reviews

Food

7.2

Overall

7.8

Comfort

7.7

Crew

8.4

Boarding

7.8

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.
Finnair
7.6
Good
1,292 reviews
KLM
7.8
Good
1,363 reviews

Food

7.2

Overall

7.8

Comfort

7.7

Crew

8.4

Boarding

7.8

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.
SWISS
7.5
Good
1,632 reviews
KLM
7.8
Good
1,363 reviews

Food

7.2

Overall

7.8

Comfort

7.7

Crew

8.4

Boarding

7.8

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.
United Airlines
7.4
Good
8,809 reviews
KLM
7.8
Good
1,363 reviews

Food

7.2

Overall

7.8

Comfort

7.7

Crew

8.4

Boarding

7.8

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.
Turkish Airlines
7.3
Good
3,853 reviews
KLM
7.8
Good
1,363 reviews

Food

7.2

Overall

7.8

Comfort

7.7

Crew

8.4

Boarding

7.8

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.

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.

  • What are the cheapest airlines to fly from Chicago to Estonia one-way?

    The cheapest airlines for a one-way flight from Chicago to Estonia are SWISS ($393), Turkish Airlines ($401), and Scandinavian Airlines ($521).

  • 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 $986). 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

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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 junho 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$414Average$460FlexibilityNo cancel feeOn-time77%
FinnairCheapest$513Average$760FlexibilityNo cancel feeOn-time76%
United AirlinesCheapest$528Average$680FlexibilityNo cancel feeOn-time69%
LufthansaCheapest$539Average$744FlexibilityNo cancel feeOn-time76%

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