On-the-fly
Where next from Chicago?
Mid-trip and figuring out the next stop? Pick your travel-time budget and vibe shift, we'll rank destinations that fit.
Loading…
Travel time
Vibe shift
Focus on
Country
Budget
Group
Top picks from Chicago
Toronto
Canada909h drive or 1.9h flight · 701 km · quick flight
New York City
United States89~2.4h flight · 1,144 km · quick flight · same country
Cape Cod
United States89~2.8h flight · 1,435 km · quick flight · same country
Milwaukee
United States882h drive or 1.2h flight · 131 km · short hop · same country
Madison
United States872h drive or 1.2h flight · 196 km · short hop · same country
Nantucket
United States87~2.8h flight · 1,457 km · quick flight · same country
Quebec City
Canada86~2.8h flight · 1,413 km · quick flight
Pittsburgh
United States868h drive or 1.8h flight · 659 km · quick flight · same country