Travelers have found it’s best to book a flight 40 days in advance to save up to 99% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 40 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Estonia 1-2 weeks in advance for as low as $769, or $806 for flights within the next 24 hours.
Flights from Chicago to Estonia lean towards being more expensive in July. Prices are generally better when you fly from Chicago to Estonia in January, with the cheapest ticket starting at $464.
When flying from Chicago to Estonia, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$515 - $967
Route
Depart
Return
Price
Chicago O'Hare IntlTallinn Ulemiste
ORD - TLL
ORDTLL
Chicago O'Hare Intl
Wed 10/23
2 stops20h 40m
Tallinn Ulemiste
Mon 10/28
2 stops30h 20m
Chicago O'Hare IntlTallinn Ulemiste
ORD - TLL
ORDTLL
Chicago O'Hare Intl
Sun 8/11
1 stop10h 40m
Tallinn Ulemiste
Wed 10/2
2 stops18h 05m
Chicago O'Hare IntlTallinn Ulemiste
ORD - TLL
ORDTLL
Chicago O'Hare Intl
Sun 8/11
2 stops39h 15m
Tallinn Ulemiste
Wed 10/2
2 stops29h 04m
Chicago O'Hare IntlTallinn Ulemiste
ORD - TLL
ORDTLL
Chicago O'Hare Intl
Wed 7/24
2 stops25h 30m
Tallinn Ulemiste
Wed 8/21
2 stops25h 25m
Chicago O'Hare IntlTallinn Ulemiste
ORD - TLL
ORDTLL
Chicago O'Hare Intl
Sat 7/20
2 stops37h 45m
Tallinn Ulemiste
Tue 8/20
2 stops25h 34m
Chicago O'Hare IntlTallinn Ulemiste
ORD - TLL
ORDTLL
Chicago O'Hare Intl
Mon 7/22
1 stop12h 10m
Tallinn Ulemiste
Tue 8/20
1 stop33h 10m
Chicago O'Hare IntlTallinn Ulemiste
ORD - TLL
ORDTLL
Chicago O'Hare Intl
Thu 10/24
1 stop38h 15m
Tallinn Ulemiste
Mon 10/28
1 stop38h 05m
Chicago O'Hare IntlTallinn Ulemiste
ORD - TLL
ORDTLL
Chicago O'Hare Intl
Mon 6/3
1 stop22h 10m
Tallinn Ulemiste
Tue 6/18
1 stop14h 05m
Chicago O'Hare IntlTallinn Ulemiste
ORD - TLL
ORDTLL
Chicago O'Hare Intl
Wed 6/5
1 stop12h 50m
Tallinn Ulemiste
Thu 6/13
1 stop21h 45m
No data available for this route at this time. Please check back soon.
Entertainment
Crew
Boarding
Overall
Comfort
Food
Reviews
Flight was delayed 2 hours due to technical issues they were having at Zurich airport according to the swiss agent when I called. This caused my connection flight to be unviable. The swiss agent was helpful in finding me a partner airline to fulfill my need to get to final destination in eastern Europe. However, the only flight the agent was originally able to find me was a connecting flight through Frankfurt with a 7 hour layover and not only that but they didnt have space on the flight without upgrading me to a higher cabin class at my expense of 384 euro. I asked if this could be waived since the technical issues were not my fault from the beginning and the agent stated they arent. I ended up paying the extra 384 euro for the agent to call me back an hour later stating he found another flight through Munich with only an hour and a half layover which was great, but when I asked for the 384 euros to be refunded he stated that was included in the price difference for this flight and there was nothing he could do about that. I feel like I got scammed out of that 384 euros as that was a cabin upgrade for a flight I never ended up taking that was supposed to be my replacement for an error they were having on their end. I am grateful for the agent finding me replacement flights that worked in my favor time wise but not in being swindled out of extra charges. I also paid 85 USD to "pick my seats" (which honestly feels like a cash grab on behalf of airlines these days anyways) on my original swiss flight that I did not receive back either since I could not pick my seats on the replacement flights as well. Way to use flight delays for swindling your customers Swiss. Kayak was great as usual but I did not have any communications with Kayak directly for this ordeal it was all through Swiss airlines.
Entertainment
Crew
Boarding
Overall
Comfort
Food
Reviews
Flight was delayed 2 hours due to technical issues they were having at Zurich airport according to the swiss agent when I called. This caused my connection flight to be unviable. The swiss agent was helpful in finding me a partner airline to fulfill my need to get to final destination in eastern Europe. However, the only flight the agent was originally able to find me was a connecting flight through Frankfurt with a 7 hour layover and not only that but they didnt have space on the flight without upgrading me to a higher cabin class at my expense of 384 euro. I asked if this could be waived since the technical issues were not my fault from the beginning and the agent stated they arent. I ended up paying the extra 384 euro for the agent to call me back an hour later stating he found another flight through Munich with only an hour and a half layover which was great, but when I asked for the 384 euros to be refunded he stated that was included in the price difference for this flight and there was nothing he could do about that. I feel like I got scammed out of that 384 euros as that was a cabin upgrade for a flight I never ended up taking that was supposed to be my replacement for an error they were having on their end. I am grateful for the agent finding me replacement flights that worked in my favor time wise but not in being swindled out of extra charges. I also paid 85 USD to "pick my seats" (which honestly feels like a cash grab on behalf of airlines these days anyways) on my original swiss flight that I did not receive back either since I could not pick my seats on the replacement flights as well. Way to use flight delays for swindling your customers Swiss. Kayak was great as usual but I did not have any communications with Kayak directly for this ordeal it was all through Swiss airlines.
Entertainment
Crew
Boarding
Overall
Comfort
Food
Reviews
Flight was delayed 2 hours due to technical issues they were having at Zurich airport according to the swiss agent when I called. This caused my connection flight to be unviable. The swiss agent was helpful in finding me a partner airline to fulfill my need to get to final destination in eastern Europe. However, the only flight the agent was originally able to find me was a connecting flight through Frankfurt with a 7 hour layover and not only that but they didnt have space on the flight without upgrading me to a higher cabin class at my expense of 384 euro. I asked if this could be waived since the technical issues were not my fault from the beginning and the agent stated they arent. I ended up paying the extra 384 euro for the agent to call me back an hour later stating he found another flight through Munich with only an hour and a half layover which was great, but when I asked for the 384 euros to be refunded he stated that was included in the price difference for this flight and there was nothing he could do about that. I feel like I got scammed out of that 384 euros as that was a cabin upgrade for a flight I never ended up taking that was supposed to be my replacement for an error they were having on their end. I am grateful for the agent finding me replacement flights that worked in my favor time wise but not in being swindled out of extra charges. I also paid 85 USD to "pick my seats" (which honestly feels like a cash grab on behalf of airlines these days anyways) on my original swiss flight that I did not receive back either since I could not pick my seats on the replacement flights as well. Way to use flight delays for swindling your customers Swiss. Kayak was great as usual but I did not have any communications with Kayak directly for this ordeal it was all through Swiss airlines.
Entertainment
Crew
Boarding
Overall
Comfort
Food
Reviews
Flight was delayed 2 hours due to technical issues they were having at Zurich airport according to the swiss agent when I called. This caused my connection flight to be unviable. The swiss agent was helpful in finding me a partner airline to fulfill my need to get to final destination in eastern Europe. However, the only flight the agent was originally able to find me was a connecting flight through Frankfurt with a 7 hour layover and not only that but they didnt have space on the flight without upgrading me to a higher cabin class at my expense of 384 euro. I asked if this could be waived since the technical issues were not my fault from the beginning and the agent stated they arent. I ended up paying the extra 384 euro for the agent to call me back an hour later stating he found another flight through Munich with only an hour and a half layover which was great, but when I asked for the 384 euros to be refunded he stated that was included in the price difference for this flight and there was nothing he could do about that. I feel like I got scammed out of that 384 euros as that was a cabin upgrade for a flight I never ended up taking that was supposed to be my replacement for an error they were having on their end. I am grateful for the agent finding me replacement flights that worked in my favor time wise but not in being swindled out of extra charges. I also paid 85 USD to "pick my seats" (which honestly feels like a cash grab on behalf of airlines these days anyways) on my original swiss flight that I did not receive back either since I could not pick my seats on the replacement flights as well. Way to use flight delays for swindling your customers Swiss. Kayak was great as usual but I did not have any communications with Kayak directly for this ordeal it was all through Swiss airlines.
Entertainment
Crew
Boarding
Overall
Comfort
Food
Reviews
Flight was delayed 2 hours due to technical issues they were having at Zurich airport according to the swiss agent when I called. This caused my connection flight to be unviable. The swiss agent was helpful in finding me a partner airline to fulfill my need to get to final destination in eastern Europe. However, the only flight the agent was originally able to find me was a connecting flight through Frankfurt with a 7 hour layover and not only that but they didnt have space on the flight without upgrading me to a higher cabin class at my expense of 384 euro. I asked if this could be waived since the technical issues were not my fault from the beginning and the agent stated they arent. I ended up paying the extra 384 euro for the agent to call me back an hour later stating he found another flight through Munich with only an hour and a half layover which was great, but when I asked for the 384 euros to be refunded he stated that was included in the price difference for this flight and there was nothing he could do about that. I feel like I got scammed out of that 384 euros as that was a cabin upgrade for a flight I never ended up taking that was supposed to be my replacement for an error they were having on their end. I am grateful for the agent finding me replacement flights that worked in my favor time wise but not in being swindled out of extra charges. I also paid 85 USD to "pick my seats" (which honestly feels like a cash grab on behalf of airlines these days anyways) on my original swiss flight that I did not receive back either since I could not pick my seats on the replacement flights as well. Way to use flight delays for swindling your customers Swiss. Kayak was great as usual but I did not have any communications with Kayak directly for this ordeal it was all through Swiss airlines.
Entertainment
Crew
Boarding
Overall
Comfort
Food
Reviews
Flight was delayed 2 hours due to technical issues they were having at Zurich airport according to the swiss agent when I called. This caused my connection flight to be unviable. The swiss agent was helpful in finding me a partner airline to fulfill my need to get to final destination in eastern Europe. However, the only flight the agent was originally able to find me was a connecting flight through Frankfurt with a 7 hour layover and not only that but they didnt have space on the flight without upgrading me to a higher cabin class at my expense of 384 euro. I asked if this could be waived since the technical issues were not my fault from the beginning and the agent stated they arent. I ended up paying the extra 384 euro for the agent to call me back an hour later stating he found another flight through Munich with only an hour and a half layover which was great, but when I asked for the 384 euros to be refunded he stated that was included in the price difference for this flight and there was nothing he could do about that. I feel like I got scammed out of that 384 euros as that was a cabin upgrade for a flight I never ended up taking that was supposed to be my replacement for an error they were having on their end. I am grateful for the agent finding me replacement flights that worked in my favor time wise but not in being swindled out of extra charges. I also paid 85 USD to "pick my seats" (which honestly feels like a cash grab on behalf of airlines these days anyways) on my original swiss flight that I did not receive back either since I could not pick my seats on the replacement flights as well. Way to use flight delays for swindling your customers Swiss. Kayak was great as usual but I did not have any communications with Kayak directly for this ordeal it was all through Swiss airlines.
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