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Short getaways in Chicago – a 48-hour tour of shopping, sightseeing and deep dish pizza

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You can get only a glimpse of the city on a short getaway in Chicago. With just a few nights in a Chicago hotel, follow our exciting itinerary and see the city’s best.

Chicago short getaway day one, morning

Kick off your short getaway in Chicago by the Michigan Avenue bridge for an Architecture River Tour. Knowledgeable guides pepper the cruise with historical details, iconic structures like the neo-Gothic Tribune Tower and the soaring, 108-story Sears Tower. Amble along bustling Michigan Avenue, pausing to marvel at Millennium Park’s dramatic Frank Gehry-designed pavilion. Stop inside the nearby Beaux-Arts Chicago Cultural Center for a look at the sweeping white Italian marble staircase.

Start: Michigan Avenue and Wacker Drive
Nearest El station: Randolph Street

Afternoon

Grab a seat and rest your feet for lunch on the large patio at Park Grill in Millennium Park. Take in a panoramic view of the Chicago skyline or look east at the glistening blue waters of Lake Michigan. Then head back on to Michigan Avenue to indulge in some world-class shopping. The wide streets make window-shopping easy at designer boutiques like Burberry or Ferragamo.

Start: Park Grill, Millennium Park
Nearest El station: Randolph Street

Evening

After a brief respite at your Chicago hotel, satisfy your early evening appetite with a sauce-and-cheese-filled deep dish pizza at a Gino’s or Pizzeria Uno. Then head to Buddy Guy’s Legends, west of Grant Park, for authentic blues – and maybe even a set by the namesake blues legend himself. Or check out Kingston Mines, where music drips like honey from the fingertips of local musicians.

Start: Park Grill, Millennium Park
Nearest El station: Randolph Street 

Chicago short getaway day two, morning

Start your second day exploring one or two of Chicago’s finest museums. Try the Art Institute of Chicago for its collection of 20th-century European paintings and Himalayan art. The Field Museum of Natural History, a few miles southeast on the shoreline, holds the largest Tyrannosaurus Rex fossil ever discovered. Or take a virtual reality trip into the outer reaches of the galaxy at the Adler Planetarium. 

Start: Art Institute of Chicago 
Nearest El station: Adams Street 

Afternoon

Take the brown El train line up to Armitage Avenue and spend a leisurely afternoon strolling fashionable Lincoln Park. Start with a burger and cold drink at John Barleycorn, a relaxing neighborhood pub. Browse the smattering of clothing boutiques, coffees shops and bookstores south on Halsted Street, Clark Street and Armitage Avenue. Learn about Chicago’s gangster past at the Chicago History Museum, or come face to face with the gorillas, the star attraction at Lincoln Park Zoo. 

Start: John Barleycorn 
Nearest El station: Fullerton Avenue 

Evening

End your Chicago short getaway on the Near North side with a juicy steak at Mike Ditka’s Restaurant. Then taxi over to Second City, the comedy club where Tina Fey got her first laughs. If the Chicago Cubs are in town, a hot dog, a cold beer and a bleacher seat at Wrigley Field tops off a perfect evening. 

Start: Mike Ditka’s Restaurant 
Nearest El station: Chicago Avenue