Believe it or not, I’ve never been to Chicago! A visit to family this fall finally brought me to the Midwest, with enough time leftover for a long weekend in the Windy City. Although the city is absolutely full of bucket list restaurants that I’d kill to dine in, I’m sadly on a tight budget this time so I’ll be checking out ways to experience Chicago on the cheap. I’ve got to leave something for next time, I suppose!

You can see most of these tips on a map view with my Chicago Foursquare list handiest with the Foursquare app but can also be viewed on the web. Scroll to the bottom of this page for a Chicago-specific Twitter feed for the latest happenings around town.

>> Visit my Chicago Photo Galleries.

Map of Chicago

Things to Do in Chicago

  • Millenium Park – Lots of things to do at this public park, besides visiting Cloud Gate, better known as “the Bean”.
  • Chicago Greeters – FREE tours of 2-4 hours on a variety of neighborhoods or interests can be scheduled if you book at least 10 days in advance, or drop in on the free InstaGreeter tours of the Loop, Millenium Park, Uptown and Hyde Park. Tours follow a strict no-tip policy and even include your public transport if needed!
  • Hot Tix – half price theater tickets on the day of the show
  • Architecture Boat Tour – People describe this as a “must do” but if you’re on a budget, at least be sure to catch the Chicago Water Taxi. An all day pass is $8 on weekdays and $10 on weekends. We caught it from Michican Avenue south to Chinatown for dim sum and back, but during the week you can also head north. Chicago’s skyline is beautiful viewed from its waterways!
  • Second City – improv comedy theater

Where & What to Eat in Chicago

  • Deep Dish Pizza – Lou Manalti’s
  • Chicago Dog – Portillo’s is one of the most famous spots for a Chicago Dog or an Italian Beef sandwich!
  • Garrett Popcorn
  • Revival Food Hall – a food court with a good selection of local chefs and popular vendors all under one roof downtown. They’re busy with downtown workers at lunch but also stay open for happy hour at the bar.
  • The Girl and the Goat
  • Alinea
  • Next
  • The Aviary
  • Publican
  • Rooftop bar @ the Wit
  • Intelligentsia Coffee
  • Sunda
  • HB
  • Mon Ami Gabi
  • San Soo Gab San Korean
  • Ras Dashen Ethiopian
  • Tango Sur

Chicago Resources

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