Plan a Summer Long-Weekend in Chicago

Chicago is a perfect long weekend getaway destination, especially during summer.

Memorial Day weekend kicks off the summer; it’s the weekend that restaurants (that haven’t already) open up their outdoor patios and roofdecks, when summer festivals take over the social calendar and farmers markets spring up in every neighborhood, and when Chicago beaches officially open for business.

Fourth of July brings the massive Taste of Chicago food and entertainment festival, while Labor Day is a bittersweet last hurrah before the cold of winter.

If you’re planning a long-weekend trip to Chicago, whether it be for an official three-day holiday weekend or at any time, we have plenty of resources to help you plan the perfect vacation. You can even combine a trip to Chicago with some Midwest weekend getaways to lesser known, but very worthwhile smaller towns in the region, like New Buffalo in Michigan, Lake Geneva in Wisconsin, and Galena in Illinois.

If your travels will keep you in the big city, check out our 3-day itinerary for Chicago, search for hotel deals in Chicago, and search for cheap flights to Chicago – but don’t forget that bus and train are affordable options in the area as well.

Photo by Luiz Felipe Castro