Cheap trips from Chicago

A week under $1,500 from Chicago.

From Chicago, 63 destinations fit a full week under $1,500, airfare plus seven days on the ground. It starts at Mérida, about $585 all in. $1,500 also reaches Bridgetown, Barcelona and Anchorage. Just over the line: Goa at $1,506.

Prices updated 2026-06-07.

Every week under $1,500 from Chicago

Mérida, Mexicoflight $235 + $50/day for a week$585
Guatemala City, Guatemalaflight $295 + $45/day for a week$610
Oaxaca, Mexicoflight $269 + $55/day for a week$654
Mexico City, Mexicoflight $257 + $65/day for a week$712
Medellín, Colombiaflight $415 + $50/day for a week$765
Bogotá, Colombiaflight $393 + $55/day for a week$778
San Juan, Puerto Ricoflight $138 + $100/day for a week$838
Cartagena, Colombiaflight $320 + $75/day for a week$845
Puerto Vallarta, Mexicoflight $250 + $90/day for a week$880
San José, Costa Ricaflight $417 + $80/day for a week$977
Tbilisi, Georgiaflight $776 + $35/day for a week$1,021
Lima, Peruflight $608 + $60/day for a week$1,028
Las Vegas, United Statesflight $122 + $130/day for a week$1,032
Kraków, Polandflight $662 + $55/day for a week$1,047
Cancún, Mexicoflight $286 + $110/day for a week$1,056
Delhi, Indiaflight $824 + $35/day for a week$1,069
Sofia, Bulgariaflight $772 + $45/day for a week$1,087
Warsaw, Polandflight $670 + $60/day for a week$1,090
Cairo, Egyptflight $744 + $50/day for a week$1,094
Belgrade, Serbiaflight $754 + $50/day for a week$1,104
Austin, United Statesflight $230 + $130/day for a week$1,140
Budapest, Hungaryflight $687 + $65/day for a week$1,142
Orlando, United Statesflight $102 + $150/day for a week$1,152
Chiang Mai, Thailandflight $875 + $40/day for a week$1,155
Montego Bay, Jamaicaflight $322 + $120/day for a week$1,162
Yerevan, Armeniaflight $883 + $40/day for a week$1,163
Prague, Czechiaflight $679 + $70/day for a week$1,169
Hanoi, Vietnamflight $908 + $40/day for a week$1,188
Ho Chi Minh City, Vietnamflight $875 + $45/day for a week$1,190
Rio de Janeiro, Brazilflight $565 + $90/day for a week$1,195
Roatán, Hondurasflight $721 + $70/day for a week$1,211
Punta Cana, Dominican Republicflight $315 + $130/day for a week$1,225
San Diego, United Statesflight $248 + $140/day for a week$1,228
Bangkok, Thailandflight $892 + $50/day for a week$1,242
Panama City, Panamaflight $717 + $75/day for a week$1,242
Tunis, Tunisiaflight $892 + $50/day for a week$1,242
Manila, Philippinesflight $917 + $50/day for a week$1,267
Zagreb, Croatiaflight $787 + $70/day for a week$1,277
Kuala Lumpur, Malaysiaflight $904 + $55/day for a week$1,289
Istanbul, Turkeyflight $805 + $70/day for a week$1,295
Naples, Italyflight $700 + $85/day for a week$1,295
Ljubljana, Sloveniaflight $785 + $75/day for a week$1,310
Kathmandu, Nepalflight $1,071 + $35/day for a week$1,316
Porto, Portugalflight $759 + $80/day for a week$1,319
Cusco, Peruflight $865 + $65/day for a week$1,320
Casablanca, Moroccoflight $906 + $60/day for a week$1,326
Nassau, Bahamasflight $284 + $150/day for a week$1,334
Berlin, Germanyflight $655 + $100/day for a week$1,355
Athens, Greeceflight $733 + $90/day for a week$1,363
Phuket, Thailandflight $875 + $70/day for a week$1,365
Lisbon, Portugalflight $701 + $95/day for a week$1,366
Bali, Indonesiaflight $985 + $55/day for a week$1,370
Buenos Aires, Argentinaflight $881 + $70/day for a week$1,371
Split, Croatiaflight $674 + $100/day for a week$1,374
Antalya, Turkeyflight $957 + $60/day for a week$1,377
Marrakech, Moroccoflight $928 + $65/day for a week$1,383
Los Cabos, Mexicoflight $265 + $160/day for a week$1,385
Madrid, Spainflight $643 + $110/day for a week$1,413
Taipei, Taiwanflight $895 + $75/day for a week$1,420
Amman, Jordanflight $946 + $70/day for a week$1,436
Bridgetown, Barbadosflight $429 + $150/day for a week$1,479
Barcelona, Spainflight $648 + $120/day for a week$1,488
Anchorage, United Statesflight $373 + $160/day for a week$1,493

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