Sightseeing: Chicago


I guess I officially live in this city now, since I just completed my first weekend of hosting a friend from home! I don’t think we could have packed much more into this weekend, so I’m recapping here to provide (1) A personal recollection for my own reference and (2) Ideas for anyone else hosting/visiting the Windy City. Some of these pursuits can be enjoyed at little/no cost; others require some deal hunting and advance planning. A combination of spontaneity and street smarts makes for a perfect weekend!

Millennium Park and Gardens: Filled with sculptures, fountains, and wildflowers, the gardens around Millennium Park and the Art Institute offer spectacular views of the city amidst relative seclusion. Walk over the BP Pedestrian Bridge for some really breathtaking sights. b4
Navy Pier: If you are up for a walk, the journey from Millennium Park to Navy Pier can be a beautiful and surprisingly quiet trip through the coveted Streeterville neighborhood. Check out the tourist hotspots, including dining at Bubba Gump Shrimp Co., Margaritaville, Harry Caray’s, Riva, and City Porch. I especially enjoy riding the Ferris Wheel, which offers a constant rotating view of the Chicago skyline. Great shows can also be found at the IMAX theater and at Chicago Shakespeare Theater (Who wants to see King Lear with Larry Yando this fall? This girl!). The Smith Museum of Stained Glass is also a beautiful sight to behold.
Oak Street Beach: Walking northbound from Navy Pier, you get sand, surf, and refreshments. What more do you need?
Magnificent Mile: We traversed that stretch at least four times, hitting Water Tower Place, H&M, F21, Nike, Express, Giordano’s Pizza, Ghirardelli Chocolate, and the Cheesecake Factory. I’m currently enjoying leftovers from the last one…delicious. b3
Chicago Architecture Tour: A plethora of boats offers amazing river views and insightful commentary on Chicago history and architecture (I suggest buying in advance and checking GoldStar for discounts from the Chicago Architecture Foundation). We used Shoreline Sightseeing on Friday night and enjoyed light breezes and amazing views of the city lights.

Lincoln Park Zoo: It’s free, and did I mention, it’s free? This city paradise is not only a great bargain, but a great stimulation for the senses as you admire beautiful creatures surrounded by calming landscapes. On our visit, some of the animals were snoozing in the summer heat, but we got quite an aquatic show from Anana the polar bear. b2
Chicago Air and Water Show: Every August, the city is stormed by a flurry of aircraft. Enjoy the show from the gardens near Lincoln Park Zoo (surprisingly not crowded at all), or brave the crowd crush at North Avenue Beach, where the essence of the show can be had. Check out the Chicago-based Boeing tent for cool merchandise, slather on the SPF, and grab a cold one. The day features stunt aircraft, P-51s and historical planes, the U.S. Army Golden Knights parachute team, and the headliners: the U.S. Navy Blue Angels. It’s a thrill to see (and hear) them buzz through the city canyons on their practice passes preceding the show, but the experience of a direct flyover from only a few hundred feet up…whoa.
Chicago History Museum: Always nice to get some background on your surroundings, a trip to this institution provides great perspectives on Chicago’s beginnings, challenges, and triumphs. On this visit, I paid special attention to the new exhibit on photographer Vivian Maier and the display on my very own neighborhood landmark, the Edgewater Beach Hotel. Also, look for coverage of the 1933 World’s Fair (we tend to forget about that one, but it was completely stunning).
Old Town: Great shopping (String a Strand!), great food (Topo Gigio!), great company!
The Second City: Catch a show if you can– and buy in advance. Tickets are quick to sell out (Hot Tix offers good deals).
Hancock Tower Signature Room: To cap off the day, head back down to the Mag Mile and straight up to the 95th floor of this landmark for vibrant atmosphere and unbeatable views.

Vintage Garage:
Hop on the Red Line and get off at the Argyle stop to partake in a treasure trove of vintage Americana. Occurring every third Sunday of the month, the Vintage Garage features dozens of vendors and hundreds of finds.
The Cheesecake Factory: Located in the lower level of the Hancock Tower, the food and atmosphere are the tops.

I just finished my slice of Godiva cheesecake… I think I need to sleep this one off. Until next time, friends!



  1. And you wonder why I’m a confirmed, 3rd generation Chicagoan!? Well done. Next visit, get a car and drive up to see the Bahai Temple, on Sheridan Road, pretty much across the street from where we spent the summer! Beyond words.


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