Chicago Recommendations

Things to Do

1. This is one of the greatest food cities in the world. Every cuisine you can imagine, ranging from dirt cheap to high end molecular gastronomy (expensive, but worth it) world class restaurants. yelp is your friend. I can also provide a ton of recommendations.
   1. Some unique Chicago foods to try
      1. Chicago style pizza – I like Pequods. Many love Lou Malnati’s or any of these
      2. Chicago style hot dog – You definitely need to grab a char dog at the Wiener’s Circle after midnight on a saturday.
      3. Chicago Italian Beef
      4. Jibarito sandwich at the Jibarito stop or Jibaritos Y Mas
   2. Some classics
      1. Great burgers
      2. Great fried chicken – the Roost, Parson’s (enjoy it with a Negroni slushy on the back patio in Logan Square), and many others 
2. Music is everywhere.
   1. Chicago Blues should be experienced, but there is every genre playing live somewhere. For Blues, I like Rosa’s, B.L.U.E.S on Halsted, Blue Chicago, Kingston Mines, Buddy Guy’s, etc. 
   2. For jazz, poetry slams and Chicago history, go to the Green Mill. I love the Gypsy Jazz there on Wednesdays.
   3. Plenty of nightclubs for dancing
   4. I also love SoFAR Sounds Chicago for intimate music concerts in people’s homes.
3. Summertime is amazing. It makes the shitty ridiculously long winter weather worth it. Festivals all the time.
   1. The lakefront. Everyone is out doing everything. Walk, bike, rollerblade along the lake.
   2. Festivals and events every week
   3. Free movies, concerts and tai chi, yoga, pilates, and zumba at Millennium Park. 
   4. Free movies in other parks in the city
   5. Summer Dance. free dance lessons then put it into practice
   6. Lincoln Park Zoo – the oldest FREE zoo in the US
4. Beaches. We got ’em. No seriously, here are 24 of them! Catch rays, play beach volleyball, swim in freezing water. Go to the Air and Water Show in August
5. Walk all over. This is a city of neighborhoods. Here is a less editorialized guide
6. Theater
   1. Broadway in Chicago for large scale (and expensive) shows, but check out HotTix for ½ price tickets
   2. The Infinite Wrench (previously known as Too Much Light Makes the Baby Go Blind) by the NeoFuturists – absolutely love this. I always take my guests here. so Chicago. creative small theater at its best. A VERY unique and fun show.
   3. Burlesque shows
   4. Comedy
      1. Chicago invented and does long form improv really well. 
      2. I personally like the fast pace and energy of short form though. 
      3. Second City is famous, of course. 
      4. Regular standup at the Beat Kitchen on Tuesday nights is only $5 for a great show from Chicago Underground Comedy
   5. Storytelling: like This American Life, but with booze – Story Lab, This Much is True, The Moth, 
7. Bars – this town likes to drink. I like to join this town in drinking.
   1. I prefer cool, sexy, chill lounges and speakeasy types places like Violet Hour, Scofflaw, Untitled (with a fun free burlesque show on Thursdays and over 500 whiskeys). 
   2. Chicago’s storied history includes the speakeasy, small hidden bars.
   3. see the city lights from rooftop bars. 
   4. If you want to pay way too much for an admittedly very cool cocktail experience and snooty staff, check out Aviary. 
8. Architecture tours – I LOVE THESE, especially the kayaking
   1. Architectural Boat Tours or walking tours. 
   2. It’s also a cool and physically fun thing to do a Chicago River Kayak Architecture tour or Fireworks Paddle (check online for discount coupons of up to 50% off…). 
9. More Touristy stuff – Sears Tower (yes, that is what you should call it) or John Hancock Observatory (better yet – don’t pay for that and go to the 95th floor for a cocktail instead – same view…) 
10. World class museums – Art Institute. Science and Industry (my fav). Field Museum. Shedd Aquarium. Adler Planetarium. Museum of Contemporary Art. Plus lots more… Some days certain museums are free.
11. The CityPass is a also good deal if you are going to do a lot of touristy stuff.
12. Watch sports – Cubs, White Sox, Blackhawks, Bulls, Bears
13. Divvy bikes and e-scooters all over the city – ride along the lakefront
14. More FREE STUFF!

More References for Things to Do

1. timeout chicago
2. Thrillist
3. the chicago reader
4. Choose Chicago
5. Chicago Magazine Restaurant Hot List

2022 Summer Festival Calendar