Please don't go to Navy Pier.
  1. Go on an architecture tour
    My favorite is through the Chicago Architecture Foundation. Have a drink, sit back, and learn a little bit about our beautiful city.
  2. Eat classic Chicago foods
    You must get the Chicago Classic at Lou Malnatis. Even if you think you don't like deep dish. Also try the hot dog and chocolate cake shake at Portillo's.
  3. Dine at some of the best restaurants in the country
    Stay tuned for a list of @sarahgorman and my favorites. If you have to pick one, make it The Purple Pig.
  4. Have a drink with a view
    Skip the Willis/Sears Tower and go to the Signature Room at the Hancock and pay for a drink rather than an elevator ticket. Head to the J. Parker for some amazing views of Lincoln Park or Cindy's for views of Millennium Park.
  5. Pretend you're in paradise
    You didn't think you were going to go to a tropical island on this trip, did you? Check out a tiki bar like Three Dots and a Dash or Lost Lake.
  6. Play a drinking game
    Play bocce or pool at The Game Room at The Chicago Athletic Association. Giant jenga at Streeter's. Curling at Kaiser Tiger. Chicagoans love to mix competition and drinking.
  7. Catch a ball game
    Even if you don't like baseball, you'll enjoy a day at historic Wrigley Field.
  8. Grab a six pack and eat at a BYOB
    There are so many of these in Chicago and it provides for some excellent cost savings along with your delicious meal. My favorites are Toro, Tango Sur, Chilam Balam, and The Angry Crab.
  9. Hang out at a museum
    The Field Museum, The Art Insititute, The Shedd Aquarium. They have these types of museums in every major city so it's not my first choice but these are nice ways to spend the day.
  10. Laugh at a world class comedy show
    Seriously guys, the mainstage shows always exceed my expectations. You might see someone who will be on SNL one day.
  11. Tour a brewery
    Lagunitas is awesome. You can also check out Goose Island or Revolution.
  12. Drink at an Irish pub
    Someone told me that Chicago has more bars per square mile than Ireland. I don't know if that's true, but you should still check out River Shannon. They have free popcorn, giant jenga, and are dog friendly.
  13. Take your new profile picture at The Bean
    I don't care how cliche this is. It's fun and you have to do it.
  14. Explore a park
    Lincoln Park is beautiful and the zoo is free! Millenium Park is funky and modern. There are so many more.
  15. Live that patio lifestyle
    So many patios to drink on, so little time. I like The Dawson, Homeslice, Parlor, Gaslight, and Big Star.
  16. Sneak into a speakeasy
    Some are harder to get into than others. The Office, Violet Hour, The Drifter, The Library, Watershed.
  17. Go on a food tour
    I recommend Chicago Food Planet and Chicago Detours.
  18. Let someone spit on you
    These things are so weird. I can't even. Don't really do this.
  19. Enjoy a beer and bacon tasting
    Thoughtfully paired and curated. Paddy Long's.
  20. Watch some fireworks
    Every Wednesday and Saturday night in the summer.
  21. Go to the "beach"
    I'm from Massachusetts so I don't count Lake Michigan's shores as a true beach, but it ain't too shabby.
  22. See a Broadway show
    So many things preview here before they go to New York or come here on tour.
  23. Shop til you drop
    Sure you can go to your typical mall stores on The Magnificent Mile or window shop in The Gold Coast, but you can also buy exotic spices and oils in Old Town.
  24. Explore the riverwalk
    This is brand new and such a nice stroll or spot to grab a drink.
  25. Hang out in a mansion
    Restoration Hardware has transformed the historic Three Arts Club into a showroom and cafe.
  26. Catch a movie in the park
    And bring wine. There are hundreds of these in the summer. Particularly great if you can catch one set in Chicago like Ferris Bueller or The Blues Brothers.
  27. Move here
    Seriously, I'm an east coast girl at heart but this city is clean, beautiful, walkable, has everything you could ever want AND rent is way more affordable than New York, Boston, San Fran, etc. It's the best of all worlds!