$516+ Cheap flights from Tallinn (TLL) to Chicago (CHI)
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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
TLL — CHI
Oct 5 — Oct 121
Round-trip
1 adult, Economy
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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
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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
Best
Last-minute
One-way
Cheapest flights from Tallinn to ChicagoExplore 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 September 5, 2026.
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 September 5, 2026.
This LOT deal was found by Cheapflights users on 9/3. 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 LOT is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:05 pm -
1 stop13h 50m
Tue 11/39:50 pm -
1 stop31h 35m
Deal found 9/3![LOT logo]()
$516
This Booking.com deal was found by Cheapflights users on 9/1. 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.
Sun 10/46:00 am -
1 stop19h 50m
Mon 10/199:30 pm -
1 stop19h 20m
Deal found 9/1![Finnair logo]()
$567
This Scandinavian Airlines deal was found by Cheapflights users on 9/1. 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.
Sat 10/3111:10 am -
1 stop13h 35m
Tue 11/37:15 pm -
2 stops20h 50m
Deal found 9/1![Scandinavian Airlines logo]()
$568
This FlightHub deal was found by Cheapflights users on 9/2. 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 12/206:25 pm -
2 stops33h 30m
Mon 1/119:50 pm -
1 stop19h 55m
Deal found 9/2![LOT logo]()
$614
Best flights from Tallinn to ChicagoDiscover carefully curated flight deals from Tallinn to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 5, 2026.
Discover carefully curated flight deals from Tallinn to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 5, 2026.
This Scandinavian Airlines deal was found by Cheapflights users on 9/1. 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.
Sat 10/3111:10 am -
1 stop13h 35m
Tue 11/37:15 pm -
2 stops20h 50m
Deal found 9/1![Scandinavian Airlines logo]()
$568
This Expedia deal was found by Cheapflights users on 9/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:00 am -
1 stop19h 50m
Mon 10/194:26 pm -
2 stops15h 19m
Deal found 9/1![Finnair logo]()
$576
This Finnair deal was found by Cheapflights users on 9/2. 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.
Sun 12/205:50 am -
2 stops17h 40m
Mon 1/115:10 pm -
2 stops21h 05m
Deal found 9/2![Finnair logo]()
$649
Last-minute flights from Tallinn to ChicagoDiscover last-minute flight deals from Tallinn to Chicago. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from Tallinn to Chicago. Data last updated September 5, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 9/1. 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.
Sun 10/46:00 am -
1 stop19h 50m
Mon 10/199:30 pm -
1 stop19h 20m
Deal found 9/1![Finnair logo]()
$567
This LOT deal was found by Cheapflights users on 9/3. 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 LOT is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:05 pm -
1 stop13h 50m
Tue 11/39:50 pm -
1 stop31h 35m
Deal found 9/3![LOT logo]()
$516
This Scandinavian Airlines deal was found by Cheapflights users on 9/1. 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.
Sat 10/3111:10 am -
1 stop13h 35m
Tue 11/37:15 pm -
2 stops20h 50m
Deal found 9/1![Scandinavian Airlines logo]()
$568
One-way flights from Tallinn to ChicagoSearch for one-way flight options from Tallinn to Chicago. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
Search for one-way flight options from Tallinn to Chicago. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Sun 10/186:00 am -
1 stop19h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![American Airlines logo]()
$563
This British Airways deal was found by Cheapflights users on 9/1. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1810:10 am -
2 stops20h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![British Airways logo]()
$569
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 September 5, 2026.
Round-trip from | $516 (LOT) |
|---|---|
Popular in | June |
Cheapest in | April |
Average price | $539 |
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 7,457,451 searches. Data last updated September 5, 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
Cheapest round-trip
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Sat 10/31
11:10 am-5:45 pm
1 stop13h 35m
Chicago O'Hare Intl
Tue 11/3
7:15 pm-12:05 am
2 stops20h 50m
$568
Quickest round-trip
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Sun 10/18
10:10 am-10:10 pm
2 stops20h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$569
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Sun 10/4
6:00 am-5:50 pm
1 stop19h 50m
Chicago O'Hare Intl
Mon 10/19
4:26 pm-3:45 pm
2 stops15h 19m
$576
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Sun 12/20
5:50 am-3:30 pm
2 stops17h 40m
Chicago O'Hare Intl
Mon 1/11
5:10 pm-10:15 pm
2 stops21h 05m
$649
Sorted by cheapest first
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.
TLL-CHI
TLL-ORD
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
TLL-CHI
TLL-ORD
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 $458). Flying from Tallinn to Chicago in June is currently the most expensive (average of $880). 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?
Airfare is typical for this route at the moment.
Tallinn to Chicago flights typically cost between $468 and $623 in October.The cheapest round-trip price found within the last 5 days was $516 on LOT (Oct 31-Nov 3).
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 73 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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 5, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Tallinn and Chicago flights
Browse other Tallinn and Chicago flight options. Last updated on September 5, 2026.
Popular flight searches
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Top airline flying from Tallinn to Chicago
Discover the top airline that operate flights from Tallinn to Chicago. 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 7,457,451 searches. Data last updated September 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$548 | Average$770 | FlexibilityNo cancel fee | On-time76% |