Cheap trips from Chicago
A week in Guatemala City costs less than a week in Honolulu.
Total trip cost, airfare plus a week on the ground, not just the fare. That's the number that actually decides where you can afford to go.
You’re on the list. We’ll send Chicago’s cheapest trips weekly.
The cheapest weeks from Chicago
Ranked by what the whole week actually costs. A cheap flight to an expensive city loses to a pricier flight somewhere your money goes further.
- 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
Farther than you think, cheaper than you’d guess
Every one of these overseas weeks comes in under a week in Honolulu ($1,891, all in). Distance is not the same as price.
- Tbilisi, Georgiaflight $776 + $35/day for a week$1,021
- Kraków, Polandflight $662 + $55/day for a week$1,047
- 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
Whatever you’re after
The cheapest week, all in, for each kind of trip.
- BeachA week in San Juan, $838
- FoodA week in Mérida, $585
- NightlifeA week in Medellín, $765
- NatureA week in San José, $977
- HistoryA week in Mérida, $585