431 € Cheap Flights from Tallinn to Chicago

Compare Tallinn to Chicago flight deals

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

Book the best Chicago fare with no extra fees

Flight deals from Tallinn to Chicago

Looking for a cheap last-minute deal or the best return flight from Tallinn to Chicago? 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 January.

Tallinn to Chicago: Flight information

The things to know before you go.
Cheapest flight found431 €
Cheapest month to flySeptember

Finding cheap flights from Tallinn to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Tallinn to Chicago is 431 €. 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 431 €.
As of February 2026, there are no flights flying from Tallinn to Chicago.
The cheapest month to fly from Tallinn to Chicago is usually September.
If you're flying from Tallinn Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from 431 €.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Tallinn Airport to Chicago on Wednesday, 30 September 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 February, the average temperature is usually around -2°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, Finnair offers the cheapest flight tickets to Chicago.

Travelling from Tallinn Airport (TLL) to Chicago: what you need to know

  • Chicago is seven hours behind Tallinn, where Tallinn Airport is located. Chicago observes the UTC-5 timezone.

  • For a stress-free journey, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This will give you plenty of time to catch your TLL to Chicago flight.

  • Delays at security and check-in are likely if you're travelling during high season, so give yourself even more breathing space. A good general rule for peak times? Get there up to four hours early for international flights and at least two hours for domestic departures.

  • The journey from central Tallinn to TLL takes about 55 minutes by public transport. If you ride-share, drive or grab a cab, you'll cover the 5 kilometres in 15 minutes or so, depending on traffic conditions.

  • Want an easy start to your travels? Stay near TLL. Whether you have an early flight from Tallinn Airport to Chicago or just don't like being rushed, these hotels are just the thing:

  • Of all flights leaving Tallinn Airport, 66.86% arrive as scheduled at their destination.

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

  • The best price we've found for a one-way Tallinn Airport to Chicago flight is 222 €. The cheapest price for a return flight is 431 €. Keep in mind fares may change due to demand at the time of booking.

  • Don't wait until the last moment. You're more likely to pick up cheap flights from TLL to Chicago if you book early. Airlines often have some fantastic early bird discounts.

  • Finding cheap tickets from Tallinn Airport to Chicago is more likely if you can be flexible with your travel dates. Use the 'Whole month' search function to get the lowest fares throughout the month and walk away with a fantastic deal.

  • Finding a cheap flight from TLL to Chicago is a breeze with Price Alerts. All you need to do is create one of these automatic notifications and we'll let you know when a deal gets even better.

  • Find an affordable flight from Tallinn Airport to Chicago with the help of our filters. Select your ideal times, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to the centre of Chicago takes around 35 minutes by car. The centre is roughly 40 kilometres away.

  • Getting there on public transport will take you around 55 minutes.

  • If you're coming in on a late flight from Tallinn Airport to Chicago, few things beat the convenience of staying close to the terminal. Grab your luggage from the carousel and then be showered and relaxing soon after at one of these hotels near ORD:

  • Grab an O'Hare International Airport rental car and explore Chicago and beyond with your own set of wheels. Routes Car Rentals, Dollar and Budget are top providers you can book with here.

  • To get the lowest price, reserve your ride from O'Hare International Airport about four weeks in advance of your flight from TLL to Chicago.

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

Chicago Midway International Airport (MDW)

  • Central Chicago is located around 19 kilometres from Chicago Midway International Airport (MDW). Once your flight from Tallinn Airport to Chicago has landed and you've made your way through the terminal, the drive should be around 20 minutes.

  • If you travel by public transport, you'll reach the centre in 45 minutes or so.

  • There are some comfortable places to call home for the night near MDW. Tuck yourself in and get cosy after your TLL to Chicago flight at one of these well-located options:

  • The quickest way to get to where you're going is with a Chicago Midway International Airport rental car. Grab a set of wheels from Dollar, Hertz or Budget and hit the road in a heartbeat.

  • Lock in the best price by booking your ride from MDW four weeks ahead of time. You'll also have access to a wider selection of vehicles.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Hop off your flight from Tallinn Airport to Chicago and head for your hotel or jump right into exploring. The centre of Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 25 minutes to drive there.

  • If you're travelling on public transport, expect a journey of around 4 hours 15 minutes.

  • Enjoy a restful, unhurried start to your break by staying at a hotel near RFD after your TLL to Chicago flight. Recover from a day of travel or simply give yourself time to get your bearings in a new city at:

  • Whether you'd like a zippy compact for a solo getaway or a spacious SUV to fit a group of friends, you'll find the ideal Chicago Rockford International Airport rental car for you. Explore the range of wheels available here from companies such as Budget, Alamo and National.

  • If you prefer a particular kind of vehicle, booking early increases your chances of getting exactly what you want. Book your ride from RFD at least a couple of weeks ahead of your flight from Tallinn Airport to Chicago.

  • Chicago Rockford International Airport's street address is 2 Airport Cir.

Best time to go to Chicago

  • Before you book your flights from Tallinn Airport to Chicago, consider which time of year works best for you. Peak season in Chicago offers a bustling atmosphere and plenty to do, while the off-season brings better deals on hotels and smaller crowds.

  • Before locking in your Tallinn Airport to Chicago plane ticket, think about what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • If you want to travel in 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

  • Start your Chicago trip off on the right foot by choosing the perfect place to stay. Once you've booked your flight from Tallinn Airport to Chicago, explore our selection of accommodation options including:

  • There are so many things to discover in this city it can be hard to work out where to start. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are popular attractions which should feature on every Chicago itinerary.

Explore more of United States

  • You've visited Chicago, now it's time to explore other parts of United States. Travel about 451 kilometres south-east to Columbus to check off its leading attractions. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, there's plenty to keep you busy.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. No visit is complete without checking out The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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