Cheap flight tickets from Chicago to Tallinn

Compare Chicago to Tallinn flight deals

Find the cheapest month or even day of the year to fly to Tallinn

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Flight deals from Chicago to Tallinn Airport

Looking for a cheap last-minute deal or the best return flight from Chicago to Tallinn Airport? If you want to travel next month, return fares start from RM2,499. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Tallinn

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

Chicago to Tallinn: Alternative routes

Compare routes from Chicago to Tallinn below. You may find an airport to fly into that's cheaper, faster, or easier than Tallinn.

Chicago to Tallinn: Flight information

The things to know before you go.
Cheapest flight foundRM1,801
Cheapest month to flyJanuary

Finding cheap flights from Chicago to Tallinn: Frequently asked questions

The best price we found for a return flight from Chicago to Tallinn is RM1,804. 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 Chicago to Tallinn. But we found flights with one stop from RM1,804.
As of March 2026, there are no flights flying from Chicago to Tallinn.
The cheapest month to fly from Chicago to Tallinn is usually January.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Tallinn Airport on Tuesday, 12 January 2027.
No airlines currently offer direct flights between Chicago and Tallinn Airport. 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 Tallinn 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 Tallinn is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Tallinn is Scandinavian Airlines .

Flying from Chicago to Tallinn Airport (TLL): What you need to know

  • Put your holiday plans into action by working out where you'll catch your flight from Chicago to Tallinn Airport (TLL). O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the main airports in Chicago.

  • Tallinn Airport is located in Tallinn. The city is in the UTC+2 timezone and is seven hours ahead of Chicago.

  • Leave plenty of time to catch your flight from Chicago to TLL. As a general rule, arrive two hours before international departures and an hour ahead for domestic flights.

  • Delays at check-in and security are likely if you're jetting off during high season, so give yourself a bit more breathing room. The recommendation for peak periods? Arrive up to four hours early for international flights and at least two hours for domestic departures.

Airports in Chicago

O'Hare International Airport (ORD)

  • We make it easy to find cheap flights from Chicago to TLL with a stopover. To explore all your options departing from O'Hare International Airport (ORD), deselect 'Direct flights only.' Next, select a flight that has a stop long enough to tour your chosen city. Some popular stopovers between ORD and TLL include:

    • Copenhagen Airport (CPH)

    • Brussels Airport (BRU)

    • Helsinki-Vantaa Airport (HEL)

  • ORD is about 40 kilometres from central Chicago. If you're catching a cab, ride-sharing or driving from the centre, it'll take you 35 minutes or so to get there, depending on the traffic. If you're using public transport, expect the trip time to be around 55 minutes.

  • In search of a comfortable hotel near O'Hare International Airport? If you're catching an early flight from Chicago to Tallinn Airport, these stays will have you sleeping moments from check-in:

  • When it comes to the on-time performance of O'Hare International Airport, data shows 74.85% of flights complete their journey on time.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • You can get to MDW from the centre of Chicago in approximately 20 minutes by car (depending on traffic). The journey by public transport takes roughly 45 minutes to travel the 19 kilometres or so.

  • Start your holiday sooner with an additional night away from home. Before your Chicago to TLL flight, kick back in one of these hotels near Chicago Midway International Airport:

  • Chicago Midway International Airport has an on-time performance rate of 77.88%. This figure shows how often flights that leave from this airport arrive on schedule.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is around 137 kilometres from central Chicago. Driving from the city centre to the airport takes about 1 hour 25 minutes. If you're thinking about taking public transport, expect a journey of around 4 hours 15 minutes.

  • Set yourself up for a smooth departure — stay near Chicago Rockford International Airport and know you'll be at your gate with time to spare. Get settled at one of these hotels the day before if you're catching an early Chicago to Tallinn Airport flight:

  • The on-time performance record of RFD is 76.19%. In other words, that's how frequently flights that depart this airport reach their final stop as planned.

  • The address of Chicago Rockford International Airport is 2 Airport Cir.

About Tallinn Airport (TLL)

  • If you're coming in on a late flight from Chicago to Tallinn Airport, nothing tops the convenience of staying close to the terminal. Collect your bags from the carousel and then be showered and resting not long after at one of these hotels near TLL:

  • Grab a Tallinn Airport rental car and discover Tallinn and beyond with your own set of wheels. Green Motion, Sixt and NU Car Rentals are top providers to choose from here.

  • For the best deal, reserve your vehicle around four weeks ahead of your Chicago to Tallinn Airport flight.

Getting from Tallinn Airport (TLL) to central Tallinn

  • The centre of Tallinn is around 5 kilometres from Tallinn Airport. Journey times by car hire or cab will vary depending on traffic conditions and time of day, so do some research ahead of time.

  • If you're taking public transport, expect a journey time of about 55 minutes.

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

  • The lowest price we've found for a one-way ticket from Chicago to Tallinn Airport is RM965. For a return flight on this route, the best price is RM1,801. Depending on the availability and when you book, these fares may change.

  • Booking early is often the key to scoring a cheap flight from Chicago to TLL. Prices tend to rise as demand increases, so the closer you get to departure, the more expensive your ticket may be.

  • The 'Whole month' search tool shows you the cheapest Chicago to Tallinn Airport tickets across the month. It's a great way to snap up a bargain if your trip dates are flexible.

  • Save time searching for cheap plane tickets from Chicago to TLL by setting up a Price Alert. We'll send you an email or notification through the app when prices go down.

  • Tailor your travel plans using filters. Choose your preferred arrival and departure times, airlines and total journey duration. You can also sort your results by 'Best,' 'Cheapest' or 'Fastest' flights from Chicago to Tallinn Airport.

The best time to fly from Chicago to Tallinn Airport (TLL)

  • Think about your travel style when planning the timing of your trip. April is the quietest month to go to Tallinn. June is when most people book flights from Chicago to Tallinn Airport (TLL), which may be perfect if you enjoy travelling when it's busier.

  • Lock in a Chicago to TLL plane ticket departing in July if you want to visit the city during its warmest month. Expect temperatures in Tallinn to range from 12ºC (54ºF) to 26ºC (79ºF).

  • January has temperatures of between -13ºC (9ºF) and 3ºC (37ºF). Look for cheap tickets from Chicago to Tallinn Airport around that time if you want to travel when it's cooler.

More about Tallinn

  • Once you've booked your flight from Chicago to Tallinn Airport, choose a hotel that puts you where you want to be. Make one of these accommodation options your base for exploring Tallinn:

  • Your Tallinn visit wouldn't be complete without a bit of sightseeing. Top attractions that should be on your list include Old Town of Tallinn, Former KGB headquarters and Tallinn City Museum.

Explore more of Estonia

  • You've done Tallinn, now it's time to discover other corners of Estonia. Travel about 153 kilometres south-east to Tartu to tick off its top sights. From Tartu Free Tour to Estonian National Museum and Tartu Old City, your itinerary will be busy.

  • Narva is another sought-after destination in Estonia and is around 193 kilometres east of Tallinn. No trip is complete without a visit to Narva Castle, Narva Cascades and Narva Alexander's Cathedral.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.