Chicago, Illinois
Consider this one of the Midwest’s best-kept secrets: winter is actually the perfect time to visit Chicago. Because the Windy City’s off-season falls from early November to late March, many hip hotels like ACME and Freehand offer incredible promo deals this time of year, allowing you to stay downtown for a much smaller price tag. And while it might be too cold to dip your toes in Lake Michigan (unless you want to do the Polar Plunge), you can still hit The Beach Chicago, a free art installation at the Navy Pier, or ice skate at Maggie Daley Park for just $13 – $15. Better still, major attractions like the Skydeck have virtually no lines, so you can save on time as well.
