The cheapest destinations from Chicago right now are Miami from 71 EUR, Washington from 81 EUR, Boston from 129 EUR, New York from 153 EUR, Los Angeles from 178 EUR round-trip. Full ranked list below — Flightmussy live data, updated 2026-06-06.
The cheapest destinations from Chicago, ranked by the lowest round-trip fare Flightmussy has seen across the next ~12 months, with the cheapest month to fly each. Free, no signup. Prices last updated 2026-06-06.
| Route | From | Cheapest month | Most expensive month | Typical | Yearly swing |
|---|---|---|---|---|---|
| Chicago → Miami | 71 EUR | October 2026 | May 2027 | 195 EUR | 84% |
| Chicago → Washington | 81 EUR | October 2026 | May 2027 | 194 EUR | 70% |
| Chicago → Boston | 129 EUR | August 2026 | May 2027 | 175 EUR | 44% |
| Chicago → New York | 153 EUR | August 2026 | December 2026 | 175 EUR | 14% |
| Chicago → Los Angeles | 178 EUR | August 2026 | May 2027 | 255 EUR | 35% |
| Chicago → Toronto | 207 EUR | September 2026 | May 2027 | 278 EUR | 37% |
| Chicago → San Francisco | 211 EUR | June 2026 | December 2026 | 254 EUR | 23% |
| Chicago → Mexico City | 228 EUR | January 2027 | May 2027 | 268 EUR | 57% |
| Chicago → Vancouver | 298 EUR | September 2026 | May 2027 | 375 EUR | 46% |
| Chicago → Bogota | 340 EUR | November 2026 | May 2027 | 350 EUR | 8% |
| Chicago → Reykjavik | 472 EUR | September 2026 | June 2026 | 580 EUR | 31% |
| Chicago → Stockholm | 478 EUR | October 2026 | June 2026 | 495 EUR | 29% |
| Chicago → Gdansk | 485 EUR | November 2026 | June 2026 | 502 EUR | 38% |
| Chicago → Malaga | 487 EUR | January 2027 | June 2026 | 549 EUR | 45% |
| Chicago → Krakow | 488 EUR | January 2027 | June 2026 | 515 EUR | 37% |
| Chicago → Oslo | 488 EUR | November 2026 | June 2026 | 536 EUR | 35% |
| Chicago → Dublin | 489 EUR | February 2027 | June 2026 | 514 EUR | 37% |
| Chicago → Palma | 490 EUR | January 2027 | June 2026 | 615 EUR | 46% |
| Chicago → Rio De Janeiro | 490 EUR | November 2026 | May 2027 | 490 EUR | 31% |
| Chicago → Warsaw | 495 EUR | March 2027 | June 2026 | 522 EUR | 37% |
| Chicago → Milan | 497 EUR | January 2027 | June 2026 | 523 EUR | 28% |
| Chicago → Prague | 503 EUR | January 2027 | May 2027 | 559 EUR | 54% |
| Chicago → Porto | 504 EUR | February 2027 | June 2026 | 630 EUR | 43% |
| Chicago → Barcelona | 507 EUR | December 2026 | June 2026 | 512 EUR | 44% |
| Chicago → Madrid | 507 EUR | January 2027 | June 2026 | 513 EUR | 44% |
| Chicago → Paris | 509 EUR | September 2026 | June 2026 | 552 EUR | 33% |
| Chicago → Budapest | 510 EUR | January 2027 | June 2026 | 536 EUR | 37% |
| Chicago → Geneva | 510 EUR | January 2027 | June 2026 | 536 EUR | 39% |
| Chicago → Lisbon | 510 EUR | January 2027 | June 2026 | 589 EUR | 44% |
| Chicago → Zurich | 512 EUR | January 2027 | June 2026 | 538 EUR | 45% |
| Chicago → Copenhagen | 513 EUR | November 2026 | June 2026 | 541 EUR | 22% |
| Chicago → Brussels | 519 EUR | January 2027 | May 2027 | 569 EUR | 55% |
| Chicago → Vienna | 519 EUR | January 2027 | June 2026 | 545 EUR | 45% |
| Chicago → Rome | 520 EUR | January 2027 | May 2027 | 533 EUR | 50% |
| Chicago → Berlin | 530 EUR | November 2026 | June 2026 | 574 EUR | 38% |
| Chicago → London | 533 EUR | November 2026 | June 2026 | 538 EUR | 42% |
| Chicago → Athens | 544 EUR | November 2026 | June 2026 | 587 EUR | 45% |
| Chicago → Split | 544 EUR | October 2026 | June 2026 | 817 EUR | 47% |
| Chicago → Gothenburg | 550 EUR | September 2026 | June 2026 | 597 EUR | 20% |
| Chicago → Nice | 554 EUR | January 2027 | June 2026 | 626 EUR | 29% |
| Chicago → Seville | 560 EUR | September 2026 | June 2026 | 633 EUR | 46% |
| Chicago → Frankfurt | 561 EUR | September 2026 | May 2027 | 609 EUR | 42% |
| Chicago → Valencia | 564 EUR | September 2026 | May 2027 | 673 EUR | 51% |
| Chicago → Sao Paulo | 573 EUR | October 2026 | May 2027 | 705 EUR | 43% |
| Chicago → Munich | 579 EUR | January 2027 | June 2026 | 605 EUR | 43% |
| Chicago → Amsterdam | 580 EUR | October 2026 | June 2026 | 605 EUR | 48% |
| Chicago → Hamburg | 582 EUR | September 2026 | June 2026 | 760 EUR | 33% |
| Chicago → Manchester | 597 EUR | November 2026 | May 2027 | 652 EUR | 42% |
| Chicago → Istanbul | 606 EUR | January 2027 | June 2026 | 655 EUR | 33% |
| Chicago → Helsinki | 610 EUR | October 2026 | May 2027 | 617 EUR | 18% |
| Chicago → Delhi | 615 EUR | May 2027 | December 2026 | 763 EUR | 22% |
| Chicago → Dubrovnik | 629 EUR | August 2026 | June 2026 | 740 EUR | 33% |
| Chicago → Edinburgh | 629 EUR | January 2027 | June 2026 | 666 EUR | 42% |
| Chicago → Cairo | 643 EUR | August 2026 | June 2026 | 712 EUR | 20% |
| Chicago → Marrakech | 652 EUR | November 2026 | June 2026 | 652 EUR | 42% |
| Chicago → Casablanca | 661 EUR | October 2026 | May 2027 | 661 EUR | 42% |
| Chicago → Dubai | 661 EUR | November 2026 | June 2026 | 671 EUR | 11% |
| Chicago → Abu Dhabi | 673 EUR | November 2026 | June 2026 | 673 EUR | 30% |
| Chicago → Faro | 678 EUR | October 2026 | June 2026 | 731 EUR | 39% |
| Chicago → Tel Aviv | 680 EUR | December 2026 | June 2026 | 705 EUR | 44% |
| Chicago → Tenerife | 702 EUR | October 2026 | June 2026 | 730 EUR | 24% |
| Chicago → Mumbai | 703 EUR | September 2026 | June 2026 | 703 EUR | 26% |
| Chicago → Cologne | 738 EUR | November 2026 | June 2026 | 775 EUR | 23% |
| Chicago → Buenos Aires | 741 EUR | June 2026 | May 2027 | 804 EUR | 22% |
| Chicago → Phuket | 756 EUR | September 2026 | June 2026 | 896 EUR | 39% |
| Chicago → Doha | 765 EUR | September 2026 | April 2027 | 765 EUR | 22% |
| Chicago → Singapore | 769 EUR | September 2026 | June 2026 | 819 EUR | 22% |
| Chicago → Bangkok | 772 EUR | September 2026 | May 2027 | 807 EUR | 26% |
| Chicago → Taipei | 777 EUR | August 2026 | June 2026 | 871 EUR | 29% |
| Chicago → Kuala Lumpur | 782 EUR | September 2026 | June 2026 | 865 EUR | 37% |
| Chicago → Beijing | 840 EUR | September 2026 | June 2026 | 905 EUR | 28% |
| Chicago → Jakarta | 848 EUR | October 2026 | May 2027 | 868 EUR | 36% |
| Chicago → Bali | 852 EUR | September 2026 | June 2026 | 1012 EUR | 36% |
| Chicago → Hong Kong | 853 EUR | November 2026 | May 2027 | 853 EUR | 29% |
| Chicago → Nairobi | 857 EUR | September 2026 | July 2026 | 863 EUR | 18% |
| Chicago → Shanghai | 867 EUR | August 2026 | June 2026 | 932 EUR | 35% |
| Chicago → Seoul | 868 EUR | September 2026 | May 2027 | 1069 EUR | 59% |
| Chicago → Johannesburg | 910 EUR | September 2026 | May 2027 | 973 EUR | 51% |
| Chicago → Melbourne | 935 EUR | July 2026 | May 2027 | 1245 EUR | 32% |
| Chicago → Tokyo | 944 EUR | September 2026 | June 2026 | 1012 EUR | 25% |
| Chicago → Osaka | 947 EUR | August 2026 | May 2027 | 1077 EUR | 31% |
| Chicago → Cape Town | 995 EUR | October 2026 | May 2027 | 1108 EUR | 37% |
| Chicago → Sydney | 1120 EUR | August 2026 | May 2027 | 1129 EUR | 18% |
| Chicago → Auckland | 1173 EUR | December 2026 | March 2027 | 1423 EUR | 19% |
Fares are round-trip, in EUR, from live searches. They change constantly — click any route to search current prices.
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