You could easily spend several days, even weeks, in Chicago and not see half of what the city has to offer. Heck, I’ve lived here for years and still haven’t seen and done everything I’d like. You’ll never “see it all”, but you can see and do quite a bit in three short days. Here’s my suggested plan for a long weekend in Chicago.
Day 1 – Date Night in Chicago
After you’ve arrived, whether it be by bus, train, or plane (in which case you can easily take the el train in from the Midway or O’Hare Airport), and checked into your Chicago hotel, it’s time to hit the town.
If it’s Thursday, take advantage of the free admission offered at the Art Institute from 5pm to 8pm. Then head north on Michigan Avenue, past the designer shops, to the John Hancock Building, where you can sip a cocktail or enjoy a glass of wine as you watch the sun set over the city. If you’re on a budget, check out a BYOB restaurant. If you feel like a splurge, try one of the city’s innovative restaurants serving multi-course gastronomic tasting menus.
If heights just aren’t your thing, enjoy some live music pre- or post-dinner. During summer months, you can catch a free performance in Grant Park or at Ravinia (where you can also bring your own wine and snacks for a picnic and which is easily accessible via the Metra train). Or check out the jazz line up at the Green Mill, one of the city’s original jazz clubs.
Day 2 – High Style, Low Budget
Start your day at Grant Park. Snap pics of the Buckingham and Crowne Fountains, giggle at your distorted reflection in the Bean, and take in the city skyline from the Park. Stop for lunch at the classic Russian Tea Time restaurant, or save your calories to nibble on all the fresh free samples at the Lincoln Park Green City Market. Check out the animals at the free Lincoln Park Zoo, or head to one of the city’s many other free museums. If your visit falls during the summer, pack a picnic lunch and head to one of the beaches along Lake Michigan.
For a delicious meal that won’t break the bank, try BYOB favorite HB, Italian small plates restaurant Quartino, or one of celebrity-chef Rick Bayless’ two restaurants, Frontera Grill or Topolobampo.
Day Three – Classic Chicago
If you’re a baseball fan, you can’t leave Chicago without a day at Wrigley Field. If you’re more into culture, spend the morning at the Shedd Aquarium, where you can get up close to sea creatures like beluga whales, sharks, and dolphins, and then continue your education with visits to other museums, like the Art Museum, Field Museum or Museum of Science and Industry. When it’s lunch time, stop for a classic Chicago hot dog at Gold Coast Dogs, or fill up with a thick slice of deep-dish pizza at Pizzeria Uno or Giordano’s.
In the afternoon, take a Chicago Architecture Foundation River Cruise to go sightseeing along the Chicago River. The tour guides are all docents who can fill you in on more Chicago history than you could ever remember. From there, hop over to Navy Pier for a ride on the giant Ferris Wheel, or cap off your weekend in Chicago with a visit to the city’s most famous landmark – the Sears (now Willis) Tower.
