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Chicago Itineraries

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 2
  • 1 Explore the Art Institute.
  • 2 Have lunch at Russian Tea Time.
  • 3 Take the Loop Tour Train.
  • 4 Check out Millennium Park.
  • 5 Dine at SushiSamba Rio or Red Light.
  • Day 3
  • 1 Visit the Field Museum of Natural History, the Shedd Aquarium or both—they’re practically next door to each other.
  • 2 Have lunch at Manny’s Coffee Shop & Deli.  
  • 3 Browse the bookstores on Printers Row.  
  • Day 4
  • 1 Head to Lincoln Park and the Chicago History Museum.
  • 2 Get a real Chicago hot dog at the Vienna Beef Factory.
  • 3 Visit the meerkats at the Lincoln Park Zoo.
  • 4 Browse the boutiques around Armitage and Halsted streets.
  • 5 See a comedy show at Second City.
  • Day 5
  • 1 Eat a cinnamon roll the size of your head at Ann Sather’s in Andersonville.
  • 2 Tour Graceland Cemetery.
  • 3 Try authentic Vietnamese food at Tank Noodle.
  • 4 Stop in the Green Mill for live jazz.
  • 5 Look for eclectic treasures in Foursided, Scout and Andersonville Galleria.
  • Day 6
  • 1 Shop the Southport Corridor.
  • 2 Have lunch at the so-tacky-it’s-cool Lincoln Restaurant.
  • 3 See a game at or take a tour of Wrigley Field (both require some planning ahead).
  • 4 See a drag show with your dinner at the Kit Kat Lounge & Supper Club.
  • Day 7
  • 1 Get a massage at the Wicker Park location of Michael Anthony Salon Spa.
  • 2 Stop in mostly-vegetarian Earwax for a laid-back lunch.
  • 3 Visit Renegade Handmade for quirky crafts or Una Mae’s Freak Boutique for vintage clothing.
  • 4 Dine at Hot Chocolate.
  • 5 Sip a sidecar at The Violet Hour.

MAP OF 7 DAY ITINERARY

  • DAY 1
  • DAY 2
  • DAY 3
  • DAY 4
  • DAY 5
  • DAY 6
  • DAY 7
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