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$393+ Cheap flights from Chicago (CHI) to Estonia

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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TLL
Nov 20 — Nov 271
Thu 11/20
Thu 11/27
1 adult, Economy
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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 October 21, 2025.

This SmartFares deal was found by Cheapflights users on 10/19. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:10 amORD - TLL
2 stops24h 00mScandinavian Airlines
Tue 12/233:45 pmTLL - ORD
1 stop33h 00mScandinavian Airlines
Deal found 10/19$393
This Flightnetwork deal was found by Cheapflights users on 10/19. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/32:00 pmORD - TLL
2 stops22h 05mAir Canada
Wed 12/106:40 amTLL - ORD
2 stops16h 15mAir Canada
Deal found 10/19$439
This Booking.com deal was found by Cheapflights users on 10/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/39:55 pmORD - TLL
1 stop19h 50mLOT
Wed 12/101:25 pmTLL - ORD
1 stop14h 35mLOT
Deal found 10/19$448
This Flightnetwork deal was found by Cheapflights users on 10/19. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:20 pmORD - TLL
1 stop31h 00mScandinavian Airlines
Wed 12/107:00 amTLL - ORD
2 stops41h 45mScandinavian Airlines
Deal found 10/19$449
This oojo deal was found by Cheapflights users on 10/20. 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.
Mon 11/177:20 pmORD - TLL
2 stops20h 20mScandinavian Airlines
Mon 11/243:40 pmTLL - ORD
2 stops57h 05mScandinavian Airlines
Deal found 10/20$471
This Mytrip deal was found by Cheapflights users on 10/20. 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.
Mon 11/1712:50 pmORD - TLL
2 stops16h 05mMultiple Airlines
Mon 11/246:05 pmTLL - ORD
1 stop27h 05mMultiple Airlines
Deal found 10/20$476
This FlightHub deal was found by Cheapflights users on 10/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/237:20 pmORD - TLL
1 stop31h 00mScandinavian Airlines
Tue 12/28:00 pmTLL - ORD
2 stops28h 45mScandinavian Airlines
Deal found 10/20$477
This Gotogate deal was found by Cheapflights users on 10/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:00 amORD - TLL
2 stops28h 05mMultiple Airlines
Fri 12/126:05 amTLL - ORD
1 stop22h 00mMultiple Airlines
Deal found 10/20$481
This Booking.com deal was found by Cheapflights users on 10/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/174:20 pmORD - TLL
1 stop16h 50mLufthansa
Mon 11/246:05 pmTLL - ORD
1 stop27h 05mLufthansa
Deal found 10/20$501
This Booking.com deal was found by Cheapflights users on 10/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/228:15 pmORD - TLL
2 stops39h 50mMultiple Airlines
Tue 12/26:05 pmTLL - ORD
1 stop34h 00mMultiple Airlines
Deal found 10/20$503

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 October 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$393
(SmartFares)

Popular in

September

Cheapest in

March

Average price

$765
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 Estonia
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($113 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 21, 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

Sun 12/7

7:20 pm-3:10 pm

1 stop11h 50m

Tallinn

Tue 12/23

3:45 pm-4:45 pm

1 stop33h 00m

$431

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Wed 12/3

2:00 pm-8:05 pm

2 stops22h 05m

Tallinn

Wed 12/10

6:40 am-2:55 pm

2 stops16h 15m

$439

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Wed 12/3

9:55 pm-1:45 am

1 stop19h 50m

Tallinn

Wed 12/10

1:25 pm-8:00 pm

1 stop14h 35m

$448

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Mon 11/17

7:20 pm-11:40 pm

2 stops20h 20m

Tallinn

Mon 11/24

3:40 pm-4:45 pm

2 stops57h 05m

$471

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Sun 11/23

7:20 pm-10:20 am

1 stop31h 00m

Tallinn

Tue 12/2

8:00 pm-4:45 pm

2 stops28h 45m

$477

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Fri 12/5

8:00 am-8:05 pm

2 stops28h 05m

Tallinn

Fri 12/12

6:05 am-8:05 pm

1 stop22h 00m

$481

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Wed 3/4

7:20 pm-11:40 pm

2 stops20h 20m

Tallinn

Sun 3/8

11:00 am-5:45 pm

1 stop13h 45m

$496

ChicagoTartu

ORD - TAY

ORDTAY

Chicago O'Hare Intl

Fri 4/3

7:50 pm-2:25 pm

2 stops34h 35m

Tartu

Tue 4/7

5:40 am-6:15 pm

2 stops44h 35m

$920

ChicagoTartu

ORD - TAY

ORDTAY

Chicago O'Hare Intl

Fri 4/3

7:15 pm-2:25 pm

2 stops35h 10m

Tartu

Tue 4/7

2:50 pm-5:50 pm

1 stop35h 00m

$1,854

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Tue 10/28

5:20 pm-1:10 pm

1 stop12h 50m

$443

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

Showing 1-10 of 12 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, April is the cheapest month in which you can book a flight from Chicago to Estonia (average of $423). Flying from Chicago to Estonia in July is currently the most expensive (average of $802). 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 October 21, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 17% on flights from Chicago to Estonia by exploring options for tickets in the evening.

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 October 21, 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
1,333 reviews

Crew

8.1

Entertainment

6.9

Boarding

7.6

Comfort

7.4

Overall

7.6

Food

6.7

Reviews

1 / 20
6.0
Good

Rowland,Dec 2024

FRA - HEL

Finnair need to get a better system for boarding. Hundreds of passengers all attempting to get their boarding cards and passports checked at the gate and then get onto the aircraft is ridiculous, time consuming and frankly unfair to passengers.
Finnair
7.6
Good
1,333 reviews
Finnair
7.6
Good
1,333 reviews

Crew

8.1

Entertainment

6.9

Boarding

7.6

Comfort

7.4

Overall

7.6

Food

6.7

Reviews

1 / 20
6.0
Good

Rowland,Dec 2024

FRA - HEL

Finnair need to get a better system for boarding. Hundreds of passengers all attempting to get their boarding cards and passports checked at the gate and then get onto the aircraft is ridiculous, time consuming and frankly unfair to passengers.
Scandinavian Airlines
7.4
Good
1,535 reviews
Finnair
7.6
Good
1,333 reviews

Crew

8.1

Entertainment

6.9

Boarding

7.6

Comfort

7.4

Overall

7.6

Food

6.7

Reviews

1 / 20
6.0
Good

Rowland,Dec 2024

FRA - HEL

Finnair need to get a better system for boarding. Hundreds of passengers all attempting to get their boarding cards and passports checked at the gate and then get onto the aircraft is ridiculous, time consuming and frankly unfair to passengers.
United Airlines
7.4
Good
8,988 reviews
Finnair
7.6
Good
1,333 reviews

Crew

8.1

Entertainment

6.9

Boarding

7.6

Comfort

7.4

Overall

7.6

Food

6.7

Reviews

1 / 20
6.0
Good

Rowland,Dec 2024

FRA - HEL

Finnair need to get a better system for boarding. Hundreds of passengers all attempting to get their boarding cards and passports checked at the gate and then get onto the aircraft is ridiculous, time consuming and frankly unfair to passengers.
Lufthansa
6.8
Okay
7,509 reviews
Finnair
7.6
Good
1,333 reviews

Crew

8.1

Entertainment

6.9

Boarding

7.6

Comfort

7.4

Overall

7.6

Food

6.7

Reviews

1 / 20
6.0
Good

Rowland,Dec 2024

FRA - HEL

Finnair need to get a better system for boarding. Hundreds of passengers all attempting to get their boarding cards and passports checked at the gate and then get onto the aircraft is ridiculous, time consuming and frankly unfair to passengers.

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, Air Canada, and LOT can get you from Chicago to Estonia in just under 11h 50m. Your travel time can differ by up to 10h 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, April is the cheapest month in which you can book a flight from Chicago to Estonia (average of $423). Flying from Chicago to Estonia in July is currently the most expensive (average of $802). 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 October 21, 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%

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