A Weekend in Chicago: Top Five Things to Do

Chicago skyline at ohio beach

Whether you’re planning a vacation or you’re an area resident who is looking for new things to do, planning a weekend in Chicago is easy with the local guide from Sunrise Chevrolet. Check out our top five favorite things to do in the windy city, and start planning your weekend itinerary today!

Enjoy the Beauty of the Lakefront Trail

If you’d like to slow down and catch some breathtaking views of the city, a walk or bike ride on Chicago’s Lakefront Trail is one of the best ways to do it. This paved trail spans 18 miles from Ardmore Avenue in Edgewater and snakes right down to 71st Street, providing unrivaled views of Lake Michigan and the city skyline along the way. If you’ll be cruising on a bike, just be sure to wear the proper protective gear, and always use appropriate hand signals to let others on the trail know your next move before you do it.

Check Out the City’s Many Museums

Chicago is known for its plethora of museums that make up some of the best in the midwest. Whether you’re planning a solo trip or you’re traveling with a group of family or friends, you can easily spend the entire day at the Art Institute or the Field Museum and still not have seen every last exhibit. Other popular options include the Museum of Contemporary Art, the Adler Planetarium, and the Museum of Science and Industry.

art institute of chicago

Indulge in Classic Chicago Foods

Every big city has its culinary staples, and Chicago is no exception! After spending the day perusing museums or taking to the pavement on the Lakefront Trail, we strongly encourage you to refuel with a Chicago-style hot dog, a hearty Italian beef sandwich, or a slice of the city’s infamous deep dish pizza. Where should you go to try each of these staples? Giordano’s has been serving deep dish to Chicagoans since 1974 and is considered by many to be the number one provider. If it’s hot dogs and beef sandwiches you’re after, Portillo’s is revered as a top choice. Does your Chicago trip have you staying with family in nearby Glendale Heights? Check out some of the best halal restaurants to try out in the area.

Tour the City with an Expert Guide

New to the city? Have friends or family visiting from out of town? Guided tours are easy to plan, and they’re a reliable way to see everything the city has to offer. Sit back and relax on a Big Bus Tour, explore Chicago’s most historic buildings on a River Boat Architecture Tour, take to the lake on a Lake Michigan Sightseeing Cruise, or explore Chicago’s deep cuts on the Gangsters and Ghosts Tour.

Enjoy Chicago’s Many Festivals

No matter what weekend your Chicago trip centers around, you can almost guarantee there will be a fun festival to attend somewhere in the city – even in the winter! Indulge in the Taste of Chicago or the Windy City Smokeout in July, have a laugh at the Chicago Sketch Comedy Festival in January, or check out the Chicago International Film Festival in October.

Sunrise Chevrolet Is Your Trusted Local Guide!

Whether you need help planning a weekend in Chicago or you’re seeking trusted advice to plan a winter getaway, a road trip through Illinois, or a shopping and dining trip in Bloomingdale, Sunrise Chevrolet is here for you. Even if you’re searching for local car shows near Glendale Heights, our locally-based team has amassed plenty of community knowledge over the years, and we’re always excited to share with you! Have questions? Want to share some local tips of your own? Contact us today!


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