Itinerary: A Long Weekend in Chicago in Spring


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 hotel in River North or on the Magnificent Mile.

Day 1:

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 Field Museum, Shedd Aquarium, or Art Museum, or take  a bus south to the Museum of Science and Industry (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.

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.

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Day 2:

Here’s where 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.

But if it’s still cold and grey (or even snowing) in March or April, you’re plans 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:

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.

More on Chicago in spring

Photos by Casino JonesSergey Galyonkin, Dream Dottie