Three-Day Weekends: Chicago
Yes I have written about Chicago before, but seriously now, there is no better city to visit in the summer than sweet home
Chicago. So it is humid on some days. So Michigan Avenue is crowded with people. So getting a bleacher seat for a Cubbie game can be a small fortune. Chicago is by far one of those places that makes me smile, that gives me a craving for Old Style Light, that makes me ecstatic to wander the city streets all day, that says it is okay to shop until you drop, that even though I am looking up at skyscrapers all day my neck is feeling just fine…could I gush even more? Well, yes!
A pal of mine, Erin Montgomery, was also born in this fabulous town. We were longing for summer in Chicago back in May. We made a few calls and within days our tickets were booked for a long weekend in July. Arriving at 2am into Midway airport my friend Jim Simmons played us Skip Haynes’ song ‘Lake Shore Drive’ on the car ride home, yes a bit cheesy, but not for a die hard fan of blues, deep dish pizza and nostalgia. Gosh so where do I begin, it just might be easier to go day by day at this point:
Friday began as a marathon day. We wanted a taste of everything since we knew that the rest of the weekend was pretty
booked up seeing friends, family and a boat race. The day included: Chicago Architecture Foundation Tour, Shopping on Michigan Avenue, Field Museum of Natural History for the Darwin exhibit, Shedd Aquarium to see a friend dive in the tank, Dinner at Mon Ami Gabi, Toad the Wet Sprocket in concert at Lincoln Park Zoo, and a night cap or three at R. J. Grunts. Yes, you can do this all in one day.
Saturday we were slightly fuzzy but headed down to the riverwalk for a great lunch with Erin and Jim’s dad. It was great to see the Friends of the Chicago River Foundation and their incredible efforts to clean up the pollution in the river. We went to the bridge house museum to explore more and even saw a fish hotel. There were loads of people kayaking and canoing the river as well, a site that a decade ago wouldn’t have been as frequent. After meeting up with my brother and sister-in-law we also cruised Oak street and went and checked out the Canyon Ranch development that will add to the skyline in 2011. Speaking of new developments the only sad moment of the trip is when I saw the Trump development right on the river next to the Wrigley building, let us hope this is the first and last building he will get approval for in Chicago. After a bit of down time we met some friends at Opera, a restaurant in the south loop area. They made us duck three ways and the ambiance is incredible.
Sunday was the day we left, so sad, but we ended it well. Up bright and early and headed to the Columbia Yacht Club. This
club is housed in a historic wood and iron plated steamboat. We headed in and out to the docks where the crew of the Fine Line was getting ready for the race. After hanging on the boat and meeting the crew we said our farewells and saw them off for the days races. Then headed over to Millenium Park to see the bean, the pavillion and the other urban art throughout the park. Next was a final run over to Garrett popcorn to get some tasty morsels for folks back in San Francisco. Our car picked us up and off we were up Lake Shore Drive for the flight back to the city by the bay.
If you haven’t been to Chicago you need to put it on your list of cities to explore. If you have been, make a point to get there at least once during the summer months. San Francisco is my city, but Chicago is my hometown.
Planning a trip? Browse all of Viator’s tours and things to do in Chicago, or else Liz will be annoyed with you.
Subscribe to Viator Travel Blog now.




August 24th, 2007 at 7:22 am
Thanks for this post! I am going to Chicago this weekend and I am looking forward to some exploration time! Cheers~
August 24th, 2007 at 10:29 am
Liz - During my 8 years in Chicago, Garrett’s popcorn was a must for all my visitors to town. I was amazed…even on a blustery Chicago winter morning, people would line up outside to get it.
Good call!
Ken