Cheapest international trips from Chicago
The cheapest international week we price from Chicago is Colombia (Medellín): about $2,470 for 2 adults, 7 nights, round-trip flights from CHI included. Oaxaca (≈ $2,660) and Mexico City (≈ $2,900) follow; the cheapest in Europe is Kraków (≈ $3,550).
. Flight fares and all totals are estimates, not live pricing.
All 20 international trips from Chicago, cheapest first
Every destination is priced the same way for 2 adults: 7 nights, a mid-range room, daily costs, and round-trip economy flights from Chicago (CHI). Fares are typical round-trip ranges per person; the line under each shows where the range comes from and when it was last updated (6 of 20 routes from CHI currently use refreshed Aviasales data).
| # | Destination | All-in for 2 | Round-trip fare from CHI | Flight time |
|---|---|---|---|---|
| 1 | Colombia (Medellín) | ≈ $2,470$1,778–$3,169 | $399–$587 ppKAYAK typical, October 2026 | From about 8.5 hr with 1 stop (often via PTY or BOG) |
| 2 | Mexico (Oaxaca) | ≈ $2,660$1,822–$3,496 | $386–$663 ppKAYAK typical, October 2026 | From about 7.5 hr with 1 stop (often via MEX or DFW) |
| 3 | Mexico City | ≈ $2,900$2,027–$3,776 | $296–$523 ppAviasales cached, Oct 17, 2026 | About 4.5 hr nonstop (Aeromexico, Volaris and others) |
| 4 | Colombia (Cartagena) | ≈ $2,990$2,064–$3,910 | $367–$625 ppKAYAK typical, October 2026 | From about 8.5 hr with 1 stop (often via MIA or FLL) |
| 5 | Poland (Kraków) | ≈ $3,550$2,620–$4,475 | $673–$1,030 ppKAYAK typical, October 2026 | About 9 hr nonstop (LOT) |
| 6 | Mexico (Puerto Vallarta) | ≈ $3,870$2,898–$4,835 | $504–$720 ppKAYAK typical, October 2026 | About 5 hr nonstop (United Airlines and American Airlines) |
| 7 | Portugal (Lisbon) | ≈ $4,010$2,935–$5,076 | $680–$1,103 ppKAYAK typical, October 2026 | About 8 hr nonstop (TAP AIR PORTUGAL) |
| 8 | Mexico (Cancún) | ≈ $4,040$2,793–$5,280 | $329–$470 ppAviasales cached, Oct 17, 2026 | About 4 hr nonstop (United Airlines, American Airlines and others) |
| 9 | Hungary (Budapest) | ≈ $4,060$3,102–$5,011 | $676–$983 ppKAYAK typical, October 2026 | From about 12.5 hr with 1 stop (often via CPH or MUC) |
| 10 | Bali (Indonesia) | ≈ $4,160$3,412–$4,900 | $1,076–$1,190 ppAviasales cached, Oct 17, 2026 | From about 23 hr with 1 stop (often via AUH or HKG) |
| 11 | Thailand (Bangkok) | ≈ $4,180$3,114–$5,246 | $885–$1,328 ppAviasales cached, Oct 17, 2026 | From about 22 hr with 1 stop (often via TPE or HKG) |
| 12 | Costa Rica | ≈ $4,350$3,092–$5,604 | $461–$737 ppKAYAK typical, October 2026 | About 5 hr nonstop (United Airlines) |
| 13 | Bansko (Bulgaria) | ≈ $4,400$3,258–$5,550 | $719–$1,155 ppKAYAK typical, October 2026 | From about 13 hr with 1 stop (often via IST or WAW) |
| 14 | Barcelona | ≈ $4,690$3,337–$6,048 | $601–$1,099 ppKAYAK typical, October 2026 | About 8.5 hr nonstop (United Airlines and American Airlines) |
| 15 | Türkiye (Istanbul) | ≈ $4,890$3,800–$5,981 | $745–$1,013 ppAviasales cached, Oct 17, 2026 | About 10.5 hr nonstop (Turkish Airlines) |
| 16 | Thailand (Phuket) | ≈ $5,360$4,023–$6,698 | $979–$1,459 ppKAYAK typical, October 2026 | From about 22.5 hr with 1 stop (often via AUH or HKG) |
| 17 | London | ≈ $5,450$4,013–$6,877 | $624–$936 ppAviasales cached, Oct 17, 2026 | About 8 hr nonstop (United Airlines, British Airways and American Airlines) |
| 18 | Iceland (Reykjavík) | ≈ $6,190$4,482–$7,896 | $526–$798 ppKAYAK typical, October 2026 | About 6 hr nonstop (Icelandair and United Airlines) |
| 19 | St. Anton (Austrian Alps) | ≈ $7,110$5,199–$9,024 | $712–$1,297 ppKAYAK typical, October 2026 | About 9 hr nonstop (SWISS and United Airlines) |
| 20 | Niseko (Japan) | ≈ $7,650$5,698–$9,610 | $1,129–$1,640 ppKAYAK typical, October 2026 | From about 16.5 hr with 1 stop (often via HND or NRT) |
Cheapest by region from Chicago
- Europe (incl. Iceland and Türkiye): Poland (Kraków) at ≈ $3,550, then Portugal (Lisbon) at ≈ $4,010.
- Mexico, Central & South America: Colombia (Medellín) at ≈ $2,470, then Mexico (Oaxaca) at ≈ $2,660.
- Asia & the Pacific: Bali (Indonesia) at ≈ $4,160, then Thailand (Bangkok) at ≈ $4,180.
The spread is wide: the cheapest week (Medellín) costs about $5,200 less than the most expensive (Niseko, ≈ $7,650). The low end of the fare ranges goes from $296 per person (Mexico City) to $1,129 (Niseko).
Nonstop international options from Chicago
Of the destinations we price, 11 list a nonstop from Chicago: Mexico City (about 4.5 hr nonstop); Kraków (about 9 hr nonstop); Puerto Vallarta (about 5 hr nonstop); Lisbon (about 8 hr nonstop); Cancún (about 4 hr nonstop); Costa Rica (about 5 hr nonstop); Barcelona (about 8.5 hr nonstop); Istanbul (about 10.5 hr nonstop); London (about 8 hr nonstop); Reykjavík (about 6 hr nonstop); St. Anton (about 9 hr nonstop). The rest need at least one connection.
How Chicago fares compare with other cities
Of our 8 departure cities, Chicago has the lowest typical fare to Cancún, Reykjavík, Oaxaca and Cartagena. It isn't the most expensive departure city for any of them. (Compared by the low end of each route's typical round-trip range.)
Chicago is also one of our US destinations, so Chicago vs. Mexico City is priced as a staycation (no flight) on the US side from here.
Photos: Medellín: Juan Gómez, CC BY 2.0 · Kraków: Andrzej Otrębski, CC BY-SA 4.0 · via Wikimedia Commons · Photo credits
Abroad or at home? Results from Chicago
Across all 21 matchups, flying from Chicago: abroad is cheaper in 13, the US trip in 3, and 5 are roughly even. The five biggest swaps:
| Matchup | US trip | Abroad | Result |
|---|---|---|---|
| Park City vs. Bansko | ≈ $9,510$6,444–$12,580 | ≈ $4,400$3,258–$5,550 | Bansko ~$5,100 cheaper |
| Maui vs. Lisbon | ≈ $7,310$5,354–$9,266 | ≈ $4,010$2,935–$5,076 | Lisbon ~$3,300 cheaper |
| Aspen vs. St. Anton | ≈ $10,400$7,692–$13,106 | ≈ $7,110$5,199–$9,024 | St. Anton ~$3,300 cheaper |
| Maui vs. Bali | ≈ $7,310$5,354–$9,266 | ≈ $4,160$3,412–$4,900 | Bali ~$3,150 cheaper |
| Jackson Hole vs. Niseko | ≈ $9,790$7,554–$12,020 | ≈ $7,650$5,698–$9,610 | Niseko ~$2,150 cheaper |
Where staying in the US wins from Chicago: New York City vs. London, New Orleans vs. Barcelona, Miami vs. Phuket.
Book this trip from Chicago
Flight searches start in Chicago (CHI) for a 7-night trip for 2 adults. Partner prices are live and may differ from our estimates.
Colombia (Medellín)
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Frequently asked questions
What is the cheapest international trip from Chicago?
Of the 20 international destinations we price, Colombia (Medellín) is the cheapest all-in week from Chicago: about $2,470 for 2 adults and 7 nights, round-trip flights included ($399–$587 per person, KAYAK typical round-trip, checked October 2026). Next: Oaxaca (≈ $2,660) and Mexico City (≈ $2,900). Sample estimates, not live prices.
What is the cheapest trip to Europe from Chicago?
Poland (Kraków), at about $3,550 all-in for 2 adults ($673–$1,030 per person, KAYAK typical round-trip, checked October 2026). The low end of typical round-trip fares from Chicago to the European destinations we price runs from $526 to $745 per person.
Are there nonstop international flights from Chicago?
To the destinations we price, these list a nonstop from Chicago: Mexico City (about 4.5 hr nonstop); Kraków (about 9 hr nonstop); Puerto Vallarta (about 5 hr nonstop); Lisbon (about 8 hr nonstop); Cancún (about 4 hr nonstop); Costa Rica (about 5 hr nonstop); Barcelona (about 8.5 hr nonstop); Istanbul (about 10.5 hr nonstop); London (about 8 hr nonstop); Reykjavík (about 6 hr nonstop); St. Anton (about 9 hr nonstop). Schedules and seasonality change, so check before booking.
Is it cheaper to go abroad than to vacation in the US from Chicago?
Often. Across our 21 US-vs-abroad matchups, flying from Chicago, the international trip is cheaper in 13, the US trip in 3, and 5 are roughly even. The biggest gap is Park City vs. Bansko (~$5,100 cheaper abroad).
What is the cheapest trip to Asia from Chicago?
Bali (Indonesia), at about $4,160 for 2 adults and 7 nights with flights ($1,076–$1,190 per person, Aviasales cached fares (Travelpayouts), updated Oct 17, 2026). Flight: from about 23 hr with 1 stop.
How we priced this
Every total is 7 nights for 2 adults: round-trip economy flights for both travelers, one mid-range room, and daily food, local transport and activities for two (plus lift tickets and rentals on ski trips). Flight ranges per route come from published typical fares or, where marked "Aviasales cached", from cached fare data refreshed automatically; lodging and daily costs are the same figures used on each comparison page, where every source is listed. These are sample estimates, not live prices. Read the full methodology.