The cheapest trips from Chicago this month: October 2026
Flying from Chicago, the cheapest week abroad with fresh fare data is Colombia (Medellín) at about $2,790 for 2 adults, and the cheapest US week is New Orleans at about $3,800, flights included.
. Flight fares and all totals are estimates, not live pricing.
Download the free Chicago PDF Clickable flight links, Fares updated Oct 18, 2026, 6:00 PM PT.
We only list trips whose CHI fare comes from fresh Aviasales data, so this month's Chicago list has 7 trips abroad and 7 in the US. Routes are added automatically as fare data comes in.
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Top 7 cheapest trips abroad from Chicago
| # | Trip | All-in for 2 | CHI fare | Book |
|---|---|---|---|---|
| 1 | Colombia (Medellín)From about 8.5 hr with 1 stop | ≈ $2,790$2,022–$3,559 | $521–$782per person · Aviasales, Oct 18, 2026 | Flights |
| 2 | Mexico CityAbout 4.5 hr nonstop | ≈ $2,980$2,027–$3,926 | $296–$598per person · Aviasales, Oct 18, 2026 | Flights |
| 3 | Mexico (Cancún)About 4 hr nonstop | ≈ $4,040$2,793–$5,280 | $329–$470per person · Aviasales, Oct 17, 2026 | Flights |
| 4 | Bali (Indonesia)From about 23 hr with 1 stop | ≈ $4,160$3,412–$4,900 | $1,076–$1,190per person · Aviasales, Oct 17, 2026 | Flights |
| 5 | Thailand (Bangkok)From about 22 hr with 1 stop | ≈ $4,180$3,114–$5,246 | $885–$1,328per person · Aviasales, Oct 17, 2026 | Flights |
| 6 | Türkiye (Istanbul)About 10.5 hr nonstop | ≈ $4,890$3,800–$5,981 | $745–$1,013per person · Aviasales, Oct 17, 2026 | Flights |
| 7 | LondonAbout 8 hr nonstop | ≈ $5,450$4,013–$6,877 | $624–$936per person · Aviasales, Oct 17, 2026 | Flights |
Top 7 cheapest US trips from Chicago
| # | Trip | All-in for 2 | CHI fare | Book |
|---|---|---|---|---|
| 1 | New OrleansAbout 2.5 hr nonstop | ≈ $3,800$2,755–$4,840 | $240–$320per person · Aviasales, Oct 17, 2026 | Flights |
| 2 | Washington, D.C.About 2 hr nonstop | ≈ $4,170$3,014–$5,326 | $212–$318per person · Aviasales, Oct 17, 2026 | Flights |
| 3 | San FranciscoAbout 5 hr nonstop | ≈ $4,210$3,065–$5,350 | $220–$330per person · Aviasales, Oct 17, 2026 | Flights |
| 4 | Puerto Rico (San Juan)About 5 hr nonstop | ≈ $4,290$2,922–$5,648 | $201–$409per person · Aviasales, Oct 18, 2026 | Flights |
| 5 | Florida (Miami)About 3.5 hr nonstop | ≈ $4,310$3,094–$5,534 | $182–$282per person · Aviasales, Oct 17, 2026 | Flights |
| 6 | Los AngelesAbout 4.5 hr nonstop | ≈ $4,520$3,140–$5,896 | $135–$358per person · Aviasales, Oct 18, 2026 | Flights |
| 7 | New York CityAbout 2.5 hr nonstop | ≈ $4,970$3,666–$6,266 | $223–$333per person · Aviasales, Oct 18, 2026 | Flights |
How this list is made
Every total comes from the same cost model as our 32 head-to-head matchups: round-trip economy flights for 2 from CHI, 7 nights in a mid-range room, and daily food, local transport and activities (plus lift tickets on ski trips). Only destinations whose CHI fare range comes from fares Aviasales travelers found recently (Travelpayouts Data API, departures about 1–4 months out, updated within the last 60 days) are ranked; the list and PDF regenerate automatically whenever those fares change. Click a trip for its full breakdown and sources.
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