$301+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
TLL — CHI
Nov 2 — Nov 91
Round-trip
1 adult, Economy
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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
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 October 3, 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 October 3, 2026.
This oojo deal was found by Cheapflights users on 9/29. 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 11/198:35 pm -
2 stops28h 10m
Mon 11/237:10 pm -
2 stops16h 55m
Deal found 9/29![Scandinavian Airlines logo]()
$528
This Scandinavian Airlines deal was found by Cheapflights users on 10/1. 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 10/316:20 am -
1 stop18h 25m
Tue 11/37:10 pm -
1 stop12h 10m
Deal found 10/1![Scandinavian Airlines logo]()
$597
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 October 3, 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 October 3, 2026.
This oojo deal was found by Cheapflights users on 9/29. 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 11/198:35 pm -
2 stops28h 10m
Mon 11/237:10 pm -
2 stops16h 55m
Deal found 9/29![Scandinavian Airlines logo]()
$528
This Scandinavian Airlines deal was found by Cheapflights users on 10/2. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:20 am -
1 stop18h 25m
Tue 11/37:10 pm -
1 stop12h 10m
Deal found 10/2![Scandinavian Airlines logo]()
$597
Last-minute flights from Tallinn to ChicagoDiscover last-minute flight deals from Tallinn to Chicago. Data last updated October 3, 2026 and is based on user searches.
Discover last-minute flight deals from Tallinn to Chicago. Data last updated October 3, 2026 and is based on user searches.
This Scandinavian Airlines deal was found by Cheapflights users on 10/1. 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 10/316:20 am -
1 stop18h 25m
Tue 11/37:10 pm -
1 stop12h 10m
Deal found 10/1![Scandinavian Airlines logo]()
$597
This oojo deal was found by Cheapflights users on 9/29. 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 11/198:35 pm -
2 stops28h 10m
Mon 11/237:10 pm -
2 stops16h 55m
Deal found 9/29![Scandinavian Airlines logo]()
$528
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 October 3, 2026.
Search for one-way flight options from Tallinn to Chicago. Find affordable one-way fares based on user searches. Data last updated October 3, 2026.
This Mytrip deal was found by Cheapflights users on 10/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:50 am -
2 stops15h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Finnair logo]()
$301
This Mytrip deal was found by Cheapflights users on 9/30. 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.
Sat 12/1210:40 pm -
2 stops28h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Finnair logo]()
$303
This Finnair deal was found by Cheapflights users on 9/30. 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.
Fri 11/205:50 am -
2 stops24h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Finnair logo]()
$309
This FlightHub deal was found by Cheapflights users on 10/2. 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.
Fri 12/45:50 am -
2 stops23h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![British Airways logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 10/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:50 am -
2 stops22h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Finnair logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:50 am -
2 stops21h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Finnair logo]()
$335
This FlightHub deal was found by Cheapflights users on 10/2. 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.
Fri 12/115:50 am -
2 stops39h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![British Airways logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:50 am -
2 stops22h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Finnair logo]()
$364
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 October 3, 2026.
Round-trip from | $528 (oojo) |
|---|---|
One-way from | $301 (Mytrip) |
Popular in | June |
Cheapest in | April |
Average price | $519 |
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 October 3, 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 12/5
5:50 am-1:45 pm
2 stops15h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$301
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Sat 12/12
10:40 pm-6:45 pm
2 stops28h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$303
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Fri 12/11
5:50 am-1:45 pm
2 stops39h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$349
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Thu 12/10
11:55 am-4:59 pm
2 stops37h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$409
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Fri 11/20
11:00 pm-3:30 pm
3 stops48h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$429
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Thu 12/10
10:50 pm-3:30 pm
2 stops24h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$514
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Thu 11/19
8:35 pm-4:45 pm
2 stops28h 10m
Chicago O'Hare Intl
Mon 11/23
7:10 pm-8:05 pm
2 stops16h 55m
$528
Quickest round-trip
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Sat 12/12
7:25 am-2:25 pm
1 stop15h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$554
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Wed 12/2
7:25 am-2:25 pm
1 stop15h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-9:00 am
Nonstop0h 00m
$554
TallinnChicago
TLL Tallinn - ORD Chicago O'Hare Intl
TLLORD
Tallinn
Sat 10/31
6:20 am-5:45 pm
1 stop18h 25m
Chicago O'Hare Intl
Tue 11/3
7:10 pm-3:20 pm
1 stop12h 10m
$597
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 $459). 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 $497 and $629 in November.The cheapest round-trip price found within the last 5 days was $528 on Scandinavian Airlines (Nov 19-Nov 23).
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 45 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
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.
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Alternative routes for Tallinn to Chicago
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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 October 3, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Tallinn to Chicago by cabin class
Find flights from Tallinn to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Tallinn and Chicago flights
Browse other Tallinn and Chicago flight options. Last updated on October 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Tallinn to Chicago
Discover the top 2 airlines 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 October 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$484 | Average$902 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$548 | Average$770 | FlexibilityNo cancel fee | On-time76% |