Chicago to Anguilla
~5h Flight$26,574 – $49,826
Chicago to Al Ula
~13h Flight$126,768 – $237,690
Chicago to St. Kitts
~5h Flight$27,272 – $51,136
Chicago to Malé
~18h Flight$172,386 – $323,224
Chicago to Jackson Hole
~3h Flight$12,051 – $22,596
Chicago to Madeira
~8h Flight$57,101 – $107,064
Chicago to Aspen
~2h Flight$10,788 – $20,227
Chicago to Almaty
~13h Flight$124,693 – $233,800
Chicago to Niseko
~12h Flight$112,686 – $211,286
Chicago to Kigali
~15h Flight$148,072 – $277,634
Chicago to Turks & Caicos
~4h Flight$16,342 – $30,642
Chicago to Muscat
~15h Flight$142,311 – $266,832
Chicago to Exuma
~3h Flight$14,508 – $27,203
Chicago to Seychelles
~18h Flight$171,961 – $322,427
Chicago to Verbier
~9h Flight$86,966 – $163,062
Chicago to Bodrum
~11h Flight$109,068 – $204,502
Chicago to Da Nang
~17h Flight$158,805 – $297,760
Chicago to Bermuda
~3h Flight$14,388 – $26,978
Chicago to Ras Al Khaimah
~14h Flight$138,780 – $260,213
Chicago to Cabo San Lucas
~4h Flight$17,559 – $32,923
Chicago to Nuuk
~5h Flight$25,454 – $47,726
Chicago to Harbour Island
~3h Flight$13,338 – $25,008
Chicago to Tivat
~10h Flight$98,181 – $184,090
Chicago to Courchevel
~9h Flight$87,062 – $163,241
Chicago to Paro
~15h Flight$146,431 – $274,557
Chicago to Kilimanjaro
~16h Flight$149,646 – $280,587
Chicago to Reykjavik
~6h Flight$44,698 – $83,808
Chicago to Marrakesh
~9h Flight$63,631 – $119,307
Chicago to Zanzibar
~15h Flight$148,543 – $278,518
Chicago to Baku
~12h Flight$119,041 – $223,202
Chicago to Mykonos
~11h Flight$107,278 – $201,146
Chicago to Ibiza
~9h Flight$87,696 – $164,430
Chicago to Santorini
~11h Flight$108,328 – $203,115
Chicago to Nice
~9h Flight$88,773 – $166,449
Chicago to Palma de Mallorca
~9h Flight$88,311 – $165,583
Chicago to St Barts
~5h Flight$26,841 – $50,326
Chicago to Phuket
~18h Flight$171,074 – $320,764
Chicago to Bora Bora
~8h Flight$61,010 – $114,393
Chicago to Nantucket
~2h Flight$10,029 – $18,805
Chicago to Martha's Vineyard
~2h Flight$9,775 – $18,329
Chicago to Telluride
~3h Flight$11,481 – $21,527
Chicago to Sun Valley
~3h Flight$13,566 – $25,436
Chicago to Bozeman
~3h Flight$12,249 – $22,967
Chicago to Cape Town
~11h Flight$105,413 – $197,649
Chicago to Sharm El-Sheikh
~13h Flight$122,796 – $230,243
Chicago to Djerba
~10h Flight$99,276 – $186,143
Chicago to St Moritz
~9h Flight$88,580 – $166,088
Chicago to Barbados
~6h Flight$31,179 – $58,460
Chicago to Antigua
~5h Flight$27,746 – $52,025
Chicago to St. Lucia
~5h Flight$30,170 – $56,568