Itinerary: Visit Chicago in 3 Days

Three-day Chicago itinerary

Many visitors to Chicago choose to come for a long weekend or just three to four days. Though you’ll never see it all (and wouldn’t even if you had double that amount of time), you can still experience the best of the Windy City in a few days. What you’ll want to see and do will depend on a number of factors – your interests, your budget, and the time of year you visit. It would be impossible to provide a one-size-fits-all itinerary for springtime in Chicago, but here are some general suggestions that can be tweaked according to your tastes.

Much of the general three-day Chicago itinerary can be followed, but you’ll need to make a few modifications based on the season – you can’t exactly go picnicking in Grant Park in the middle of March. For this itinerary, we’re making a few assumptions: that you have a moderate budget, that you are visiting for three days, and that you are staying at a hotel in River North or on the Magnificent Mile.

April signifies the real start of spring in Chicago and it’s one of the best times to visit the city. Sure, sometimes the city receives a freak snowstorm or the temperatures dip back into the single digits, but for the most part, spring is a pleasant, and crowd-free (not to mention cheaper) time to explore the Windy City, and there’s plenty to see and do.

Day 1 in Chicago Highlights

Assuming you’ve landed in Chicago bright and early, check into your hotel and then start your day with a quick, cheap, and tasty lunch. Swing by Wow Bao, Potbelly, XOCO, or the massive food court at Water Tower Place before heading down Michigan Avenue. Catch a bus to the Museum Campus and spend the afternoon at the Museum of Science and Industry, Field Museum, Shedd Aquarium, or Art Museum (just check the calendar of free museum days before you plan so you can score free admission).  You could easily spend hours at each museum, so choose just one or two, or limit your visit to about an hour at each one. if you will be visiting multiple museums, compare the cost of paying admission a la carte vs buying a discount pass.

top 10 free things to do in Chicago

As night falls, you can check out Chicago’s lively theatre scene,  explore the nightlife, or sample some of the amazing food and drink options in Chicago.

Day 2 in Chicago

Here’s where the time of year really begins to play a role in your schedule. If it’s a warm day in April or May, you may want to visit one of the city’s farmer’s markets and plan a picnic in Millennium Park. You can get out on the water with the stellar Chicago Architecture Foundation River cruise, play on the carnival rides at Navy Pier, or check out the animals at the Lincoln Park Zoo.  You might have plans to go see a Chicago Cubs game, and in May, you can even take the Metra to Arlington Park to see horse races.

Chicago River cruise

But if it’s still cold and grey (or even snowing) in March or April, you’re planning will differ considerably. Today is a day to check out the rest of the city’s museums, to take a sightseeing tour shop on the Magnificent Mile, stand on the glass-bottomed ledges at the Willis Tower, or have a drink with the view at the John Hancock Building.

For dinner, go all out with a multi-course tasting meal, or check out some of the more affordable downtown dining options.

Day 3 in Chicago

With your last day in the city, get out of downtown and explore some of Chicago’s many diverse neighborhoods. Have a lazy brunch and then do some vintage shopping in Lakeview, rent a bike and ride up the Lakefront Path to the beautiful homes of Lincoln Park, or browse the indie boutiques of Bucktown and Wicker Park. Have dim sum in Chinatown, saganaki in Greektown, tamales and Mexican food in Pilsen, or Korean and Vietnamese in Uptown.  For dinner, dine BYOB at a restaurant where you can bring your own wine or beer to save money. While many of these restaurants serve low-cost international cuisine in a bare-bones atmosphere, many others offer upscale dining as well.

Lincoln Park Chicago
Lincoln Park Chicago

There are lots of free things to do in Chicago if you are not afraid to walk a little bit. Chicago has a magnificent lakefront and in the summer, you can enjoy the Chicago beaches. In addition to Lake Michigan, Chicago also has the Chicago River, which riverfront has now been developed in a nice walking trail. Chicago also has great shopping on Michigan Avenue. The Chicago Skyline is also spectacular and you can se it from Navy Pier, from the Museum Campus, or from Buckingham Fountain. But Chicago’s favorite tourist attraction is now Cloudgate also know by the locals as ‘the bean’.

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