Plan a Summer Long-Weekend in Chicago

Chicago is a perfect long weekend getaway destination, especially during summer. After five months indoors, the whole city moves outside. Restaurants open their patios and rooftops, there's a street festival somewhere nearly every weekend, and the beaches fill up. Our Chicago in summer page has the weather and packing advice. This one is about picking your weekend and filling it.

The three holiday weekends

Memorial Day kicks off the season. The Park District puts lifeguards on its beaches from the Friday before Memorial Day, the Belmont-Sheffield Music Festival in Lakeview is usually one of the first street fests, and Navy Pier starts its free summer fireworks, on Wednesdays at 9pm and Saturdays at 10pm through Labor Day weekend. The lake is still cold, though, so this is a weekend for the sand, not the water. More in Memorial Day in Chicago.

The Fourth of July brings the city's biggest free fireworks show, recently held at Navy Pier, plus neighborhood shows and parades all over the city and suburbs. It's one of the most crowded nights of the year downtown, so walk or take the train. Taste of Chicago used to run over the Fourth. It doesn't anymore. It's now a free five-day festival on Columbus Drive in Grant Park, and its dates have moved around since the pandemic, so check the city's festival dates page before you plan around it. See 4th of July in Chicago and things to do in July.

Labor Day is the last hurrah before the cold. The free Chicago Jazz Festival fills Millennium Park and the Chicago Cultural Center over the holiday weekend, and it's the last weekend with lifeguards on the beaches. Our Labor Day weekend page has more.

You don't need a holiday, either. Any Friday-to-Sunday from June to August works, and some of the best summer weekends have nothing to do with the calendar. Lollapalooza takes over Grant Park for four days in late July or early August, and the Air and Water Show fills the lakefront around North Avenue Beach in mid-August. Both are great if you're going, and both push hotel rates up if you aren't. Our events page lists the rest.

Filling three days

Start with our 3-day itinerary, which is built around a summer weekend. The outdoor stuff is what makes summer worth the higher hotel rates, so lean into it.

• A free evening concert. The Grant Park Music Festival has played free classical concerts every summer since 1935, at the Pritzker Pavilion on Wednesday, Friday and Saturday evenings. Bring a blanket and a picnic for the lawn.
• A street festival. Most ask a suggested donation at the gate. The neighborhood festivals page covers the big ones.
• The beaches. Swimming is allowed from 11am to 7pm when lifeguards are on duty. North Avenue is the party beach, Oak Street has the skyline view, and 12th Street pairs well with a museum day. Check the flag before you go in.
• A farmers market. The Green City Market in Lincoln Park runs Wednesday and Saturday mornings, and there are markets in plenty of other neighborhoods.
• The water. The Chicago Architecture Center river cruise is 90 minutes and starts at $57, and there are more ideas in ways to get out on the water.
• A Cubs game at Wrigley Field, or a drink at one of the rooftop bars or patios.

Summer afternoons bring short, loud thunderstorms more often than all-day rain. When one rolls in, the museums are the obvious place to wait it out. Our rainy day list and ways to beat the heat have backups.

Getting there and where to stay

Summer is peak season, and the big festival weekends are the most expensive of all. Book your hotel early, and if prices look high, compare the neighborhoods in where to stay in Chicago. For flights, O'Hare and Midway between them have nonstops from nearly every U.S. city, and our flights page explains who flies where. Don't forget that bus and train are affordable options in the area as well. Milwaukee, St. Louis and Detroit all have several Amtrak trains a day into Union Station. See getting to Chicago.

You can also combine a trip to Chicago with a smaller town nearby. BootsnAll's Midwest weekend getaways covers places like New Buffalo in Michigan, Lake Geneva in Wisconsin and Galena in Illinois, and our own day and overnight trips from Chicago has more.

Photo by Luiz Felipe Castro