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$332+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TLL
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
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 January 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$387
(SmartFares)

One-way from

$332
(Kiwi.com)

Popular in

September

Cheapest in

February

Average price

$593
Provider with most accurate pricing for Chicago (CHI)-Tallinn flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Tallinn flights.
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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. 10% potential increase in price ($85 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 6, 2026.

This SmartFares deal was found by Cheapflights users on 1/5. 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 2/87:10 pmORD - TLL
1 stop31h 10mScandinavian Airlines
Tue 2/243:45 pmTLL - ORD
1 stop33h 00mScandinavian Airlines
Deal found 1/5$387
This oojo deal was found by Cheapflights users on 1/6. 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.
Fri 2/67:20 pmORD - TLL
1 stop11h 50mScandinavian Airlines
Sat 2/1411:00 amTLL - ORD
1 stop13h 45mScandinavian Airlines
Deal found 1/6$395
This oojo deal was found by Cheapflights users on 1/6. 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 10/227:15 pmORD - TLL
1 stop31h 30mScandinavian Airlines
Fri 10/308:00 pmTLL - ORD
2 stops28h 45mScandinavian Airlines
Deal found 1/6$418
This oojo deal was found by Cheapflights users on 1/6. 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.
Fri 2/207:20 pmORD - TLL
2 stops31h 10mScandinavian Airlines
Fri 2/278:00 pmTLL - ORD
2 stops28h 45mScandinavian Airlines
Deal found 1/6$419
This oojo deal was found by Cheapflights users on 1/4. 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 1/297:10 pmORD - TLL
2 stops36h 30mScandinavian Airlines
Sun 2/111:00 amTLL - ORD
2 stops37h 45mScandinavian Airlines
Deal found 1/4$423
This SmartFares deal was found by Cheapflights users on 1/5. 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.
Mon 11/307:20 pmORD - TLL
1 stop31h 10mScandinavian Airlines
Mon 12/148:00 pmTLL - ORD
2 stops28h 45mScandinavian Airlines
Deal found 1/5$458
This Scandinavian Airlines deal was found by Cheapflights users on 1/4. 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.
Thu 1/227:20 pmORD - TLL
1 stop11h 50mScandinavian Airlines
Mon 1/266:25 amTLL - ORD
1 stop18h 20mScandinavian Airlines
Deal found 1/4$470
This Turkish Airlines deal was found by Cheapflights users on 1/5. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/238:20 pmORD - TAY
2 stops57h 55mTurkish Airlines
Tue 1/272:40 pmTAY - ORD
2 stops51h 25mTurkish Airlines
Deal found 1/5$967

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 January 6, 2026.
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 2/8

7:10 pm-10:20 am

1 stop31h 10m

Tallinn

Tue 2/24

3:45 pm-4:45 pm

1 stop33h 00m

$387

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Wed 2/18

7:20 pm-7:30 pm

2 stops16h 10m

Tallinn

Wed 2/25

6:25 am-4:45 pm

1 stop18h 20m

$395

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Fri 2/6

7:20 pm-3:10 pm

1 stop11h 50m

Tallinn

Sat 2/14

6:25 am-4:45 pm

1 stop18h 20m

$395

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Fri 2/20

7:20 pm-3:10 pm

1 stop11h 50m

Tallinn

Fri 2/27

11:00 am-4:45 pm

1 stop13h 45m

$418

ChicagoTartu

ORD - TAY

ORDTAY

Chicago O'Hare Intl

Fri 1/23

8:20 pm-1:00 am

2 stops44h 40m

Tartu

Tue 1/27

6:00 am-10:05 am

2 stops36h 05m

$967

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Wed 4/1

6:00 pm-12:00 pm

2 stops34h 00m

$332

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Fri 1/9

8:15 pm-10:20 am

3 stops30h 05m

$469

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Fri 1/9

9:05 pm-1:00 am

2 stops43h 55m

$484

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Sat 1/10

6:50 pm-1:00 am

1 stop22h 10m

$484

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Fri 1/9

3:20 pm-5:00 pm

1 stop17h 40m

$487

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

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 $431). Flying from Chicago to Estonia in July is currently the most expensive (average of $808). 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.

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 January 6, 2026.
Read through reviews of airlines operating flights from Chicago to Estonia, such as Finnair, United Airlines, and Scandinavian Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Finnair
7.6
Good
1,345 reviews

Food

6.7

Comfort

7.4

Overall

7.6

Entertainment

6.9

Boarding

7.6

Crew

8.2

Reviews

1 / 20
4.0
Okay

Julia,Feb 2024

JFK - HEL

The bathroom was broken, AC wasn’t working, tv wasn’t working for half the flight
Finnair
7.6
Good
1,345 reviews
Finnair
7.6
Good
1,345 reviews

Food

6.7

Comfort

7.4

Overall

7.6

Entertainment

6.9

Boarding

7.6

Crew

8.2

Reviews

1 / 20
4.0
Okay

Julia,Feb 2024

JFK - HEL

The bathroom was broken, AC wasn’t working, tv wasn’t working for half the flight
United Airlines
7.4
Good
9,138 reviews
Finnair
7.6
Good
1,345 reviews

Food

6.7

Comfort

7.4

Overall

7.6

Entertainment

6.9

Boarding

7.6

Crew

8.2

Reviews

1 / 20
4.0
Okay

Julia,Feb 2024

JFK - HEL

The bathroom was broken, AC wasn’t working, tv wasn’t working for half the flight
Scandinavian Airlines
7.3
Good
1,634 reviews
Finnair
7.6
Good
1,345 reviews

Food

6.7

Comfort

7.4

Overall

7.6

Entertainment

6.9

Boarding

7.6

Crew

8.2

Reviews

1 / 20
4.0
Okay

Julia,Feb 2024

JFK - HEL

The bathroom was broken, AC wasn’t working, tv wasn’t working for half the flight
Lufthansa
6.8
Okay
7,690 reviews
Finnair
7.6
Good
1,345 reviews

Food

6.7

Comfort

7.4

Overall

7.6

Entertainment

6.9

Boarding

7.6

Crew

8.2

Reviews

1 / 20
4.0
Okay

Julia,Feb 2024

JFK - HEL

The bathroom was broken, AC wasn’t working, tv wasn’t working for half the flight

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 Turkish Airlines can get you from Chicago to Estonia in just under 31h 10m. Your travel time can differ by up to 13h 30m. 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 $431). Flying from Chicago to Estonia in July is currently the most expensive (average of $808). 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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$433Average$523FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$528Average$680FlexibilityNo cancel feeOn-time69%
LufthansaCheapest$539Average$848FlexibilityNo cancel feeOn-time76%
FinnairCheapest$624Average$995FlexibilityNo cancel feeOn-time76%

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