Only have two days to experience the best of Chicago? For a whirlwind tour of the Windy City, here’s a fun-packed itinerary that is completely doable in 48 hours.
First Day
Morning
Start the day right with breakfast, of course. Once you step out from your Chicago vacation rental for the first bite to eat, head over to South Loop. This area is home to the Bongo Room. whose specialities include pumpkin spice or caramelized apple pancakes and killer club sandwiches.
From there, you’re steps away from the Museum Campus. Check out the giant T-Rex at the Field Museum, dip into the Shedd Aquarium, or get some stargazing in at the Adler Planetarium as you digest that morning’s feast.
Pro Tip: Order tickets online and avoid long lines.
Afternoon
Go north up Michigan Avenue and snap a selfie at the Cloud Gate (aka “the Bean”) – the city’s most iconic sculpture. From there, cross the bridge to the Magnificent Mile for seemingly unlimited shopping. When you hit E. Superior Street, flip a coin to choose between Giordano’s or Gino’s East for Chicago’s famous deep-dish pizza.
After lunch, take a quick 20-minute walk to the Navy Pier for a joyride on the Centennial Ferris Wheel, where people have been enjoying panoramic views for over a century. If you still need an adrenaline rush, try the Tilt. This glass box on the 94th floor of the John Hancock Tower tilts out over the ground 1,000 feet below. Or, chill out with a nice cocktail at the Signature Room one floor up for equally amazing views.
Evening
Kingston Mines up in Lincoln Park will get your blues fix covered. Two stages of bands, 365 days a year, play the music of the Mississippi Delta. By the time you leave, you’ll need a late-night snack at the Wiener Circle. The atmosphere here is intentionally raucous and the language foul, but it’s worth it for the show and a Chicago-style hot dog loaded with mustard, pickle, tomato, onion, and pepper toppings.
Second Day
Morning
Recover from your night with fresh-roasted coffee at Intelligentsia Millennium Coffeebar, which is arguably the chain that launched the industry’s fair trade ethic. Skip over a block or so to Garrett’s for some sweet and savory popcorn, like CheeseCorn or CaramelCrisp, to snack on while you wend your way to a Chicago Architecture Foundation boat tour. Here, you can enjoy a day on the water while learning about the city’s historic and iconic skyscrapers.
Afternoon
Back on land, head for cash-only Mr. Beef on N. Orleans Street in River North for yet another Chicago favorite: An Italian beef sandwich stuffed with slow-cooked beef and pickled veggies.
Make your way to The 606, Chicago’s elevated park that was formerly a train line. The park has an awesome cross-section of bikers, walkers, artists, musicians, and views. Take the Western Access Ramp down and spend the rest of the day exploring funky Wicker Park along N. Milwaukee and N. Damen Avenues.
Evening
You’ve hit all the highlights and your time in Chicago is coming to an end, but you have to experience two last iconic spots. Hang with the local fans at historic Wrigley Field and check off this classic baseball stadium from your bucket list. And, to leave town with a smile–or better yet, a laugh–check out Second City. Here you can check out the home of improv comedy and the launching pad for many a comedian’s career.