Tallinn to Chicago from €415
Prices last checked: 27.08.2026
QUICK OVERVIEW
Best prices 8–14 nights
Best prices 15+ nights
94 deals · from 415 €
What we typically see 699 €−41% cheaper (415 €)47 deals under 530 €Cheapest in November from 415 €
Cheapest flights September 2026
Cheapest flights October 2026
-
Tu06.1012 nightsSu18.10
724 €
-
Su11.1012 nightsFr23.10
521 €
-
Fr16.108 nightsSa24.10
430 €
-
Sa17.1014 nightsSa31.10
447 €
-
Th22.1014 nightsTh05.11
666 €
-
Sa24.1011 nightsWe04.11
748 €
-
Su25.1021 nightsSu15.11
517 €
-
Mo26.1013 nightsSu08.11
650 €
-
Mo26.1015 nightsTu10.11
651 €
-
Fr30.109 nightsSu08.11
519 €
-
Sa31.108 nightsSu08.11
426 €
Cheapest flights November 2026
Cheapest flights December 2026
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Fr04.1210 nightsMo14.12
521 €
-
Fr04.1215 nightsSa19.12
724 €
-
Su06.1218 nightsTh24.12
474 €
-
Sa12.1212 nightsTh24.12
557 €
-
Mo14.1213 nightsSu27.12
557 €
-
Tu15.1216 nightsTh31.12
501 €
-
Tu15.1218 nightsSa02.01
586 €
-
Fr18.1213 nightsTh31.12
594 €
-
Th24.129 nightsSa02.01
501 €
-
Th24.1214 nightsTh07.01
444 €
-
Th31.129 nightsSa09.01
415 €
Cheapest flights January 2027
-
Fr08.0113 nightsTh21.01
578 €
-
Fr08.0114 nightsFr22.01
578 €
-
Fr08.0115 nightsSa23.01
578 €
-
Su10.0112 nightsFr22.01
501 €
-
Su10.0113 nightsSa23.01
501 €
-
Su10.0114 nightsSu24.01
501 €
-
Su10.0115 nightsMo25.01
501 €
-
Fr15.0113 nightsTh28.01
471 €
-
Su17.0113 nightsSa30.01
501 €
-
Th21.018 nightsFr29.01
494 €
-
Su24.0113 nightsSa06.02
471 €
-
Mo25.0110 nightsTh04.02
415 €
-
Fr29.018 nightsSa06.02
415 €
-
Sa30.018 nightsSu07.02
415 €
-
Su31.0113 nightsSa13.02
471 €
Cheapest flights February 2027
-
Th04.0215 nightsFr19.02
415 €
-
Fr05.028 nightsSa13.02
415 €
-
Sa06.0212 nightsTh18.02
415 €
-
Sa06.0214 nightsSa20.02
415 €
-
Su07.0214 nightsSu21.02
415 €
-
Mo08.0219 nightsSa27.02
415 €
-
Su14.0216 nightsTu02.03
415 €
-
We17.0215 nightsTh04.03
516 €
-
Su21.0211 nightsTh04.03
501 €
-
Su21.0213 nightsSa06.03
501 €
-
Su28.0211 nightsTh11.03
488 €
Cheapest flights March 2027
-
Tu02.0311 nightsSa13.03
415 €
-
Fr05.0314 nightsFr19.03
600 €
-
Sa06.0313 nightsFr19.03
659 €
-
Su07.0311 nightsTh18.03
580 €
-
Su07.0313 nightsSa20.03
677 €
-
Fr12.038 nightsSa20.03
711 €
-
Th18.038 nightsFr26.03
530 €
-
Th18.0317 nightsSu04.04
530 €
-
Su21.0314 nightsSu04.04
661 €
-
Su21.0317 nightsWe07.04
576 €
-
Su21.0320 nightsSa10.04
576 €
Cheapest flights April 2027
-
Fr02.0415 nightsSa17.04
504 €
-
Fr09.048 nightsSa17.04
493 €
-
Su18.0411 nightsTh29.04
501 €
-
Su18.0414 nightsSu02.05
661 €
-
Mo19.0419 nightsSa08.05
751 €
-
Tu20.048 nightsWe28.04
493 €
-
Th22.0417 nightsSu09.05
606 €
-
Fr23.0420 nightsTh13.05
656 €
-
Su25.0411 nightsTh06.05
664 €
-
Su25.0418 nightsTh13.05
709 €
-
Su25.0421 nightsSu16.05
661 €
Cheapest flights May 2027
-
Su02.0521 nightsSu23.05
697 €
-
Fr07.0514 nightsFr21.05
709 €
-
Fr07.0515 nightsSa22.05
709 €
-
Su09.0512 nightsFr21.05
709 €
-
Su09.0517 nightsWe26.05
664 €
-
Mo10.0519 nightsSa29.05
709 €
-
Tu18.0512 nightsSu30.05
697 €
-
We19.0515 nightsTh03.06
741 €
-
Fr21.059 nightsSu30.05
640 €
-
Fr21.0513 nightsTh03.06
689 €
-
Mo24.0511 nightsFr04.06
660 €
Good to know!
Don’t skip the grey prices either – the gap between the cheapest (green) and a grey one is often just €30–50. Given the season and demand, those are frequently great fares too compared with normal prices or searching random dates!