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Estonia

$299+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TLL
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
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 November 10, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/9. 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.
Fri 11/1410:35 pmORD - TLL
1 stop17h 05mLufthansa
Wed 11/266:00 amTLL - ORD
2 stops20h 19mLufthansa
Deal found 11/9$509
This Kiwi.com deal was found by Cheapflights users on 11/9. 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.
Tue 11/184:20 pmORD - TLL
1 stop12h 50mLufthansa
Tue 12/26:05 pmTLL - ORD
1 stop27h 05mLufthansa
Deal found 11/9$510
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Fri 11/1410:35 pmORD - TLL
1 stop17h 05mLufthansa
Thu 11/276:20 amTLL - ORD
1 stop14h 50mLufthansa
Deal found 11/10$519
This United Airlines deal was found by Cheapflights users on 11/9. 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.
Sat 11/155:55 pmORD - TLL
2 stops35h 00mUnited Airlines
Thu 11/276:20 amTLL - ORD
1 stop14h 50mUnited Airlines
Deal found 11/9$535
This United Airlines deal was found by Cheapflights users on 11/9. 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 11/1911:00 amORD - TLL
2 stops22h 10mUnited Airlines
Thu 11/276:20 amTLL - ORD
1 stop21h 45mUnited Airlines
Deal found 11/9$539
This United deal was found by Cheapflights users on 11/9. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/192:30 pmORD - TLL
2 stops18h 40mMultiple Airlines
Thu 11/276:20 amTLL - ORD
2 stops23h 32mMultiple Airlines
Deal found 11/9$546
This Booking.com deal was found by Cheapflights users on 11/9. 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 11/104:20 pmORD - TLL
1 stop16h 50mLufthansa
Mon 11/176:05 pmTLL - ORD
1 stop27h 05mLufthansa
Deal found 11/9$549
This United deal was found by Cheapflights users on 11/9. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/159:10 pmORD - TLL
2 stops31h 45mMultiple Airlines
Thu 11/276:20 amTLL - ORD
1 stop21h 45mMultiple Airlines
Deal found 11/9$550
This Mytrip deal was found by Cheapflights users on 11/9. 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.
Tue 11/184:20 pmORD - TLL
1 stop16h 30mMultiple Airlines
Tue 12/26:40 amTLL - ORD
2 stops16h 15mMultiple Airlines
Deal found 11/9$551

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 November 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$432
(Scandinavian Airlines)

One-way from

$299
(Kiwi.com)

Popular in

September

Cheapest in

March

Average price

$591
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
One-way flight 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 November 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 November 10, 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

Fri 2/6

7:20 pm-11:35 pm

2 stops44h 15m

Tallinn

Sat 2/14

4:20 pm-4:55 pm

2 stops32h 35m

$438

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Tue 3/10

4:20 pm-1:10 pm

1 stop13h 50m

Tallinn

Wed 4/1

1:50 pm-7:55 pm

1 stop14h 05m

$487

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Tue 3/10

7:30 pm-11:55 pm

1 stop21h 25m

Tallinn

Thu 4/2

1:50 pm-7:55 pm

1 stop14h 05m

$487

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Mon 3/9

12:50 pm-5:10 pm

2 stops21h 20m

Tallinn

Fri 4/10

1:50 pm-7:55 pm

1 stop14h 05m

$487

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Mon 3/9

12:50 pm-5:10 pm

2 stops21h 20m

Tallinn

Tue 3/31

6:00 am-7:55 pm

1 stop21h 55m

$487

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Mon 3/9

7:30 pm-11:55 pm

1 stop21h 25m

Tallinn

Wed 4/8

6:10 am-7:55 pm

1 stop21h 45m

$487

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Mon 3/9

12:50 pm-5:10 pm

2 stops21h 20m

Tallinn

Wed 4/1

1:50 pm-7:55 pm

1 stop14h 05m

$487

ChicagoTallinn

ORD - TLL

ORDTLL

Chicago O'Hare Intl

Wed 3/11

6:17 pm-11:55 pm

2 stops22h 38m

Tallinn

Tue 3/31

6:00 am-12:55 pm

1 stop14h 55m

$492

ChicagoTartu

ORD - TAY

ORDTAY

Chicago O'Hare Intl

Fri 4/3

7:50 pm-12:40 am

2 stops44h 50m

Tartu

Tue 4/7

2:50 pm-6:15 pm

2 stops59h 25m

$966

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

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 $805). 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 November 10, 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 November 10, 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
1,335 reviews

Entertainment

6.9

Overall

7.6

Comfort

7.4

Food

6.7

Boarding

7.6

Crew

8.1

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
1,335 reviews
Finnair
7.6
Good
1,335 reviews

Entertainment

6.9

Overall

7.6

Comfort

7.4

Food

6.7

Boarding

7.6

Crew

8.1

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
7.4
Good
1,570 reviews
Finnair
7.6
Good
1,335 reviews

Entertainment

6.9

Overall

7.6

Comfort

7.4

Food

6.7

Boarding

7.6

Crew

8.1

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
9,012 reviews
Finnair
7.6
Good
1,335 reviews

Entertainment

6.9

Overall

7.6

Comfort

7.4

Food

6.7

Boarding

7.6

Crew

8.1

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
7,564 reviews
Finnair
7.6
Good
1,335 reviews

Entertainment

6.9

Overall

7.6

Comfort

7.4

Food

6.7

Boarding

7.6

Crew

8.1

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, United Airlines, and Turkish Airlines can get you from Chicago to Estonia in just under 13h 50m. Your travel time can differ by up to 31h. 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 $805). 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 November 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$424Average$460FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$486Average$725FlexibilityNo cancel feeOn-time76%
FinnairCheapest$513Average$763FlexibilityNo cancel feeOn-time76%
United AirlinesCheapest$554Average$680FlexibilityNo cancel feeOn-time69%

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