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Cheap Flights from Estonia to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Estonia to Chicago

Wed, Oct 21 - Wed, Oct 28
LOT Logo
2:20 pm - 3:10 pmTLL  Tallinn-ORD Chicago O'Hare Intl
32h 50m1 stop Warsaw Frederic Chopin
LOT Logo
10:50 pm - 1:25 pmORD  Chicago O'Hare Intl-TLL Tallinn
31h 35m1 stop Warsaw Frederic Chopin
$553LOT
Sat, Oct 31 - Tue, Nov 3
Scandinavian Airlines Logo
6:25 am - 5:45 pmTLL  Tallinn-ORD Chicago O'Hare Intl
18h 20m1 stop Kastrup Copenhagen
Scandinavian Airlines Logo
7:15 pm - 12:05 amORD  Chicago O'Hare Intl-TLL Tallinn
20h 50m2 stops Kastrup Copenhagen Stockholm Arlanda
$570Scandinavian Airlines
Wed, Oct 21 - Wed, Oct 28
Finnair Logo
7:25 am - 5:50 pmTLL  Tallinn-ORD Chicago O'Hare Intl
18h 25m1 stop Helsinki-Vantaa
Finnair Logo
4:25 pm - 4:55 pmORD  Chicago O'Hare Intl-TLL Tallinn
17h 30m2 stops New York John F Kennedy Intl Helsinki-Vantaa
$571Finnair
Wed, Oct 21 - Wed, Oct 28
Finnair Logo
7:25 am - 7:16 pmTLL  Tallinn-ORD Chicago O'Hare Intl
19h 51m2 stops Helsinki-Vantaa Dallas/Fort Worth
Finnair Logo
7:35 pm - 10:15 pmORD  Chicago O'Hare Intl-TLL Tallinn
19h 40m2 stops London Heathrow Helsinki-Vantaa
$577Finnair
Sat, Oct 31 - Tue, Nov 3
LOT Logo
2:05 pm - 8:55 pmTLL  Tallinn-ORD Chicago O'Hare Intl
13h 50m1 stop Warsaw Frederic Chopin
LOT Logo
9:50 pm - 1:25 pmORD  Chicago O'Hare Intl-TLL Tallinn
31h 35m1 stop Warsaw Frederic Chopin
$592LOT
Sat, Oct 31 - Tue, Nov 3
Scandinavian Airlines Logo
6:20 am - 5:45 pmTLL  Tallinn-ORD Chicago O'Hare Intl
18h 25m1 stop Kastrup Copenhagen
Scandinavian Airlines Logo
7:15 pm - 12:05 amORD  Chicago O'Hare Intl-TLL Tallinn
20h 50m2 stops Kastrup Copenhagen Stockholm Arlanda
$593Scandinavian Airlines
Thu, Oct 22 - Thu, Oct 29
Finnair Logo
11:15 pm - 3:00 pmTLL  Tallinn-ORD Chicago O'Hare Intl
23h 45m2 stops Helsinki-Vantaa London Heathrow
Finnair Logo
10:30 pm - 10:15 pmORD  Chicago O'Hare Intl-TLL Tallinn
16h 45m2 stops Paris Charles de Gaulle Helsinki-Vantaa
$599Finnair
Sat, Oct 31 - Tue, Nov 3
Scandinavian Airlines Logo
6:25 am - 5:45 pmTLL  Tallinn-ORD Chicago O'Hare Intl
18h 20m1 stop Kastrup Copenhagen
Scandinavian Airlines Logo
7:15 pm - 3:20 pmORD  Chicago O'Hare Intl-TLL Tallinn
12h 05m1 stop Kastrup Copenhagen
$615Scandinavian Airlines
Tue, Dec 15 - Wed, Jan 27
LOT Logo
2:05 pm - 7:55 pmTLL  Tallinn-ORD Chicago O'Hare Intl
13h 50m1 stop Warsaw Frederic Chopin
LOT Logo
9:50 pm - 11:40 pmORD  Chicago O'Hare Intl-TLL Tallinn
17h 50m1 stop Warsaw Frederic Chopin
$642LOT
Thu, Oct 22 - Thu, Oct 29
Multiple Airlines Logo
9:30 am - 6:15 pmTLL  Tallinn-ORD Chicago O'Hare Intl
16h 45m2 stops Gdansk Rebiechowo Reykjavik Keflavik Intl
Multiple Airlines Logo
7:30 pm - 10:30 amORD  Chicago O'Hare Intl-TLL Tallinn
32h 00m3 stops Reykjavik Keflavik Intl Gdansk Rebiechowo Kastrup Copenhagen
$690Multiple Airlines
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

To get a below average price, you should book around 7 weeks before departure, which saves you about 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low season

November
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 18% lower on average.

FAQs - booking Chicago flights

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    Chicago O'Hare Intl Airport is 16 miles from the center of Chicago.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many direct flights to Chicago O'Hare Intl Airport are there each week?

    Each week there are around 42,295 direct flights from within Estonia to Chicago O'Hare Intl Airport. The most common day for departures is Sunday, with 16% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airlines flying from Estonia to Chicago

 
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.6
FinnairOverall score based on 1430 reviews
7.7Boarding
7.4Comfort
8.2Crew
6.9Entertainment
6.7Food
Airline reviews

Finnair was ok. But some things were pretty bad: 1. Crew was not friendly, especially a crew member named, Maria. She woke me up while I was deep asleep by force just to let me know that 2 people can’t be on the same seat (my toddler and me) for sleeping. 2. There was no vegetarian option in the menu so I had to eat bread for one meal 3. They didn’t have an option for child meal

2.0 MediocreDivya, Aug 2026
Read more Finnair reviews

Finnair was ok. But some things were pretty bad: 1. Crew was not friendly, especially a crew member named, Maria. She woke me up while I was deep asleep by force just to let me know that 2 people can’t be on the same seat (my toddler and me) for sleeping. 2. There was no vegetarian option in the menu so I had to eat bread for one meal 3. They didn’t have an option for child meal

The food was delicious. There has been a major improvement here in the last few years. Excellent, friendly service. An enjoyable experience.

Awful. Delayed for unknown reason. Boarded late, part of a Tight connection ands had to go through customs and immigration. And they lost my bags.

Late, dirty cabin, charging ports broken, uncomfortable, no tomato juice, barely edible food

Flight on time, landed well ahead of schedule. Attendants were excellent and responsive

The crew was friendly, and the flight landed on time

Rude Iberia security crew at the Madrid terminal. No Iberia officials to be found to redress complaints at the gate. No supervisors. Nothing for processing upgrades at the gate Iberia app did not work to let me upgrade my options to higher classes. No water was offered on a hot day in Madrid. Madrid airport air conditioning was so weak that people were sweating. Never book on any airlines that codeshare with Iberia.

Great if not for the boarding by bus at Heathrow terminal 3. Medieval disappointing time-consuming and very hard on handicapped flyers. It was awful

Do not use KAYAK or Finair for future travel. Unless you purchase the tickets directly from the airline, you were going to have a difficult time checking in. Kayak canceled my flights twice and ended up causing great difficulty in me getting back from Europe because they double sold my tickets between American Airlines and Finair. The event caused significant delays and led to me having to rebook my flights.

It was listed on my ticket as Finnair but there was no indication that the flight was Finnair. In fact the number was even different. There were no employees there until exactly 2 hours before so we had to wait in line at Iberia and hope

Our vacation started with horribly, 48hr prior to departure SAS airline cancelled our return flight giving us little to no alternative options.

The layover was very long. Other than that, great trip so far

Elderly traveler with disability was bumped from extra legroom to economy with little legroom. He couldn’t bend his knee to fit in the seat. Very uncomfortable for a 7 hour flight and will be reported to DOT. Then the food was disgusting. Boiled chicken with boiled rice and steamed veggies. 3 slices of carrot and one broccoli. We couldn’t eat it. No salt or pepper provided. Disgusting.

My daughter always gets sick when we order the gluten free meal option. Internet didn’t work as advertised.

The flight was very cold, and the seats were rather uncomfortable. The food has been better on our other SAS experiences. Most significantly, the luggage with most of my wife's personal items and clothes didn't make the flight. Hoping for a quick resolution, but no real opportunity to speak with a Human has us concerned.

It was so hot on the plane. No air jets above the seats

Please see my comments for the flight from Chicago to Copenhagen

We were sitting in SAS plus. Super friendly, service that went above and beyond on a Full Flight too! Meals were deliscious and trays were cleared promptly. Generous drinks offered throughout the flight. Would like to suggest better movies on offer to watch.... In all genres and maybe more cooking shows? There was only 1, Nadia's Everyday Baking... Thank you

This was my first time flying SAS and used them for 4 flights. The crews, flight and communication was outstanding. I flew premium economy and was extremely impressed by their SAS lounges. I will 100% ise SAS again. Everyone was so pleasant!

little entertainment choices. Seat/bed too firm an no sleeping mat

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Gurnee
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Hammond
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Elk Grove Village
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