413 € Cheap Flights from Tallinn to Chicago

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Flight deals from Tallinn to Chicago

Looking for a cheap last-minute deal or the best return flight from Tallinn Airport to Chicago? If you want to travel next month, return fares start from 477 €. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Tallinn to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Tallinn to Chicago flights are currently cheapest in November.

Alternative Tallinn to Chicago routes

Looking for the cheapest, fastest or easiest route from Tallinn to Chicago? You could fly into the following airports instead.

Tallinn to Chicago: Flight information

The things to know before you go.
Cheapest flight found413 €
Cheapest month to flyNovember

Finding cheap flights from Tallinn to Chicago: Frequently asked questions

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
The best price we found for a return flight from Tallinn to Chicago is 413 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Tallinn to Chicago. But we found flights with one or more stops from 413 €.
As of July 2026, there are no flights flying from Tallinn to Chicago.
The cheapest month to fly from Tallinn to Chicago is usually November.
If you're flying from Tallinn Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the centre of Chicago. We've found flights into this airport from 413 €.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Tallinn Airport to Chicago on Sunday, 1 November 2026.
No airlines currently offer direct flights between Tallinn Airport and Chicago. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

In July, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Scandinavian Airlines offers the cheapest flight tickets to Chicago.

Flying from Tallinn Lennart Meri Airport (TLL) to Chicago: what you need to know

  • Chicago is eight hours behind Tallinn, where Tallinn Lennart Meri Airport is located. Chicago follows the UTC-6 timezone.

  • Leave plenty of time to get on your TLL to Chicago flight. It's generally best to arrive two hours before international departures and an hour ahead for domestic flights.

  • Flying during a peak time like June? School holidays and other popular seasons can lead to longer queues at security. Be extra cautious and get there up to four hours ahead of international flights and two hours before domestic departures.

  • TLL is around 5 kilometres from central Tallinn. If you're catching a taxi, ride-sharing or driving from the centre, it'll take you 15 minutes or so to get there, depending on the traffic. If you're planning to take public transport, expect the travel time to be around 25 minutes.

  • Searching for a hotel close to TLL? If you're catching an early flight from Tallinn Lennart Meri Airport to Chicago, these stays will put you moments from your departure gate:

  • Tallinn Lennart Meri Airport scores high marks for its on-time performance. 86% of flights that take off from TLL arrive at their destination as scheduled.

How to find the cheapest flights from Tallinn Lennart Meri Airport (TLL) to Chicago

  • 254 € is currently the best price for a one-way Tallinn Lennart Meri Airport to Chicago flight. Return plane tickets start from 413 €. These prices can change depending on demand and availability.

  • Don't leave things to the last moment. You're more likely to find cheap flights from TLL to Chicago if you book ahead. Airlines often have some amazing early bird discounts.

  • If you're willing to be flexible with your trip dates, take advantage of the 'Whole month' tool. It'll show you the cheapest price across every month when searching for a Tallinn Lennart Meri Airport to Chicago ticket.

  • Spend less time searching for cheap flights from TLL to Chicago by creating a Price Alert. You'll receive an email or notification through the app when a new low fare is offered.

  • Pick your preferred departure and arrival times, airlines and number of stops with our filters. Then, sort the results for your flight from Tallinn Lennart Meri Airport to Chicago by 'Cheapest,' 'Fastest' or 'Best.'

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) to central Chicago takes about 30 minutes by car. The centre is roughly 27 kilometres away.

  • If you're taking public transport, expect a journey time of around 45 minutes.

  • If you're arriving on a late flight from Tallinn Lennart Meri Airport to Chicago, nothing beats the convenience of staying near the terminal. Collect your bags from the carousel and then be showered and resting soon after at one of these accommodation options near ORD:

  • For the lowest price, reserve your vehicle from Chicago O'Hare International Airport around four weeks ahead of your flight from TLL to Chicago.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is located around 16 kilometres from Chicago Midway International Airport (MDW). After your flight from Tallinn Lennart Meri Airport to Chicago has landed and you've made your way out of the airport, the drive should take about 25 minutes.

  • If you're catching public transport, it'll take around 30 minutes.

  • You'll find some great places to rest your head close to MDW. Tuck yourself in and get cosy after your TLL to Chicago flight at one of these perfectly located options:

  • Get exactly what you want. Booking your ride from MDW four weeks ahead of time often means better prices and a wider choice of vehicles.

  • Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Head to the city centre after your flight from Tallinn Lennart Meri Airport to Chicago has touched down. Central Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to get to by car.

  • Public transport will get you there in about 2 hours.

  • If you don't want to travel to the centre, find a hotel close to RFD. Get comfortable at one of these options after your TLL to Chicago flight:

  • Booking a couple of weeks in advance of your flight from Tallinn Lennart Meri Airport to Chicago is a smart way to go. As well as better prices, you'll likely have a better variety of makes and models to choose from at RFD.

  • Chicago Rockford International Airport can be found at 2 Airport Cir.

Best time to go to Chicago

  • July is the most popular month for flights from Tallinn Lennart Meri Airport to Chicago. To escape the crowds, plan your trip to Chicago in January.

  • When booking your Tallinn Lennart Meri Airport to Chicago plane ticket, think about the weather you're most comfortable in. July is the warmest month in Chicago, with temperatures ranging from 16ºC (61ºF) to 28ºC (82ºF).

  • If you like cooler conditions, look for a cheap ticket from TLL to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of the United States

  • Columbus is just one of the many cities in the United States waiting to be discovered after you've experienced Chicago. Around 451 kilometres away to the southeast, top sights here include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • If you're interested in discovering another great destination in the United States, head for Indianapolis, roughly 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are the start of reasons to visit.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.