AOL Travel

Chicago in 2 days

Planning a trip to Chicago? Our experienced travel editors break down the town so you can make the most of your stay. Let these itineraries be your guide, whether you're here for a weekend or a whole week.
  • Day 1
  • 1 Get your bearings with a Chicago Architecture Foundation boat, bus or walking tour.
  • 2 Have a slice of Chicago-style pizza at Gino's Pizzeria East.
  • 3 Shop on the Magnificent Mile. Tip: You’ll find the big chains on North Michigan Avenue; the smaller, much pricier boutiques are on Oak Street.
  • 4 Dine at Frontera Grill. Get there early to avoid a long wait. If there are only two in your party, ask to eat at the bar, instead—you’ll be seated faster.
  • 5 Hop the "L" to Lincoln Parkto hear the blues at Kingston Mines.
  • Day 2
  • 1 See the dolphin show at the Shedd Aquarium.
  • 2 Pop next door to the Field Museum to visit Sue, the largest T. Rex skeleton ever found.
  • 3 Eat a pastrami-on-rye at the seriously old-school Manny’s Coffee Shop & Deli.
  • 4 Stroll around Millennium Park (in summer) or skate on its ice rink (in winter).
  • 5 Have drinks in the John Hancock Center’s 95th-floor Signature Room.  
  • 6 Splurge on filet mignon with all the fixings at the original Morton's Steakhouse.
  • 7 Go dancing at The Hangge-Uppe.    


  • DAY 1
  • DAY 2