HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$276+ Cheap flights from Tallinn (TLL) to Chicago (CHI)

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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
TLL — CHI
Jul 20 — Jul 271
Mon 7/20
Mon 7/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Tallinn to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Tallinn to Chicago

Cheapest flights from Tallinn to Chicago
Explore the most affordable flight options available from Tallinn to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 20, 2026.

This Iberia 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:55 am
TLL
-
ORD
1 stop14h 55m
Iberia
Tue 10/139:30 pm
ORD
-
TLL
1 stop10h 45m
Iberia
Deal found 6/16$491
This Iberia 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:55 am
TLL
-
ORD
1 stop14h 55m
Iberia
Wed 9/99:30 pm
ORD
-
TLL
1 stop10h 15m
Iberia
Deal found 6/17$492
This Iberia 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:55 am
TLL
-
ORD
2 stops17h 38m
Multiple Airlines
Tue 10/139:30 pm
ORD
-
TLL
1 stop10h 45m
Multiple Airlines
Deal found 6/16$496
This Iberia 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:55 am
TLL
-
ORD
2 stops16h 47m
Multiple Airlines
Wed 9/99:30 pm
ORD
-
TLL
1 stop10h 15m
Multiple Airlines
Deal found 6/17$497
This Finnair deal was found by Cheapflights users on 6/19. 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.
Wed 10/76:00 am
TLL
-
ORD
1 stop19h 50m
Finnair
Tue 10/139:30 pm
ORD
-
TLL
1 stop10h 45m
Finnair
Deal found 6/19$526
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:00 am
TLL
-
ORD
1 stop19h 50m
American Airlines
Tue 10/139:30 pm
ORD
-
TLL
1 stop10h 15m
American Airlines
Deal found 6/18$527
This Finnair 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:55 am
TLL
-
ORD
2 stops16h 47m
Finnair
Wed 9/94:01 pm
ORD
-
TLL
2 stops16h 14m
Finnair
Deal found 6/17$541

Find flight deals from Tallinn to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Tallinn (TLL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 20, 2026.

Round-trip from

$491
(Iberia)

One-way from

$276
(Booking.com)

Popular in

June

Cheapest in

April

Average price

$880
From Tallinn to Chicago (CHI)
Search Deals
One-way flight from Tallinn to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($142 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Tallinn to Chicago 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 June 20, 2026.
Use the filters below to find and compare flights from Tallinn to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 9/2

10:55 am-7:42 pm

2 stops16h 47m

Chicago O'Hare Intl

Wed 9/9

9:30 pm-3:45 pm

1 stop10h 15m

$497

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 10/7

6:00 am-5:50 pm

1 stop19h 50m

Chicago O'Hare Intl

Tue 10/13

9:30 pm-3:45 pm

1 stop10h 15m

$527

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 9/2

10:55 am-7:42 pm

2 stops16h 47m

Chicago O'Hare Intl

Wed 9/9

4:01 pm-4:15 pm

2 stops16h 14m

$541

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 10/7

10:55 am-8:33 pm

2 stops17h 38m

Chicago O'Hare Intl

Tue 10/13

9:30 pm-4:15 pm

1 stop10h 45m

$544
Quickest round-trip

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 10/7

10:55 am-5:50 pm

1 stop14h 55m

Chicago O'Hare Intl

Tue 10/13

9:30 pm-4:15 pm

1 stop10h 45m

$545

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Mon 8/3

9:25 pm-3:00 pm

2 stops25h 35m

Chicago O'Hare Intl

Mon 8/10

10:30 pm-10:50 pm

2 stops16h 20m

$585

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Mon 8/3

11:20 pm-3:00 pm

2 stops23h 40m

Chicago O'Hare Intl

Tue 8/18

9:45 pm-8:55 pm

2 stops15h 10m

$590

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 7/15

4:40 pm-3:00 pm

2 stops30h 20m

Chicago O'Hare Intl

Mon 7/20

9:30 pm-10:55 pm

1 stop17h 25m

$736
Cheapest one-way

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Wed 9/2

6:00 am-5:50 pm

1 stop19h 50m

$276

TallinnChicago

TLL - ORD

TLLORD

Tallinn

Mon 9/7

4:10 pm-5:50 pm

1 stop33h 40m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Best time to book a flight from Tallinn to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Tallinn 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 Tallinn to Chicago

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

Currently, April is the cheapest month in which you can book a flight from Tallinn to Chicago (average of $309). Flying from Tallinn to Chicago in July is currently the most expensive (average of $640). 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.

How much does it cost to fly round-trip from Tallinn to Chicago?

How far ahead should I book a flight from Tallinn to Chicago?

To ensure you get the cheapest price possible for a flight from Tallinn to Chicago, you should look to book at least 77 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Related info for your journey

Find useful and relevant information for your journey from Tallinn to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Tallinn to Chicago?

    Located just 2.1 mi from the city center, Tallinn is the airport most travelers will use when flying to Chicago from Tallinn. Booking flights from Tallinn (TLL) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 0 different airlines.

  • How long is the flight from Tallinn to Chicago?

    Airlines like American Airlines, Finnair, and Iberia fly from Tallinn to Chicago in about 14h 55m. The time it takes to get you to your destination can typically vary by up to 4h 55m. The distance from Tallinn to Chicago is about 4456 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Tallinn to Chicago (average of $309). Flying from Tallinn to Chicago in July is currently the most expensive (average of $640). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Tallinn to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Tallinn to O'Hare Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights