Cassiel & Brendan
Things To Do
Chicago Riverwalk
The Chicago Riverwalk is located walking distance from our hotel! Take a leisurely stroll on this spectacular pedestrian path along the city’s Chicago River. Observe some of the city’s gorgeous architecture and enjoy this bustling waterway full of every kind of boat imaginable. To get here from the hotel, head to the corner of W Wacker Drive and Lake Street and walk down the stairs. Coming from somewhere else? There are several entrances to the riverwalk along W Wacker Drive as you head toward the lake!
Millennium Park
Come get your requisite photo at Cloud Gate (aka The Bean), stroll through this vast, 24.5 acre beautiful park, and enjoy a snack on Lake Michigan.
The Art Institute of Chicago
Follow in the footsteps of Ferris Beuller and experience the beautiful architecture of The Art Institute. Inside, see the greatest Impressionist collection outside Paris. Stand before classics like Edward Hopper’s "Nighthawks," Seurat’s "A Sunday on La Grande Jatte," and Grant Wood’s "American Gothic."
Lakefront Trail
This epic Lake Michigan trail stretches from Hollywood Ave to 71st Street (18.5 miles!), and features glorious lakeside views. Going for a run? You’ll have plenty of company on this iconic running path - Cassiel did much of her 2024 LA Marathon training right here!
Chicago River Boat Architecture Tours
Get a front row perspective on the exquisite buildings that line the Chicago River during an architecture cruise at this most beautiful time of year. There are several options for these tours, from Chicago's First Lady River Cruises to group kayak tours (we had the best time on our kayak tour)!
Billy Goat Tavern
Enjoy a cheezburger, cheezburger from the famous John Belushi SNL sketch (or see where Brendan made Cassiel try her first - and last - pickle).
Pizzeria Uno
Chicago is famous for deep dish pizza, so check out The Original Pizzeria Uno, The Bear’s Pequod’s Pizza, Lou Malnati’s (Brendan's personal favorite), and Pizano's (right next to The Bean) …take your pick!
Willis Tower
Previously called the Sears Tower, you can experience breathtaking views of the city spanning up to four states at Skydeck Chicago, the highest observation deck in the United States atop the iconic Willis Tower.
The Magnificent Mile
Don’t miss the section of Michigan Avenue running from the banks of the Chicago River to Oak Street full of historic landmarks like the Wrigley Building, Tribune Tower, and the Chicago Water Tower as well as lots of shopping and fine dining.
Navy Pier
Take a ride on the 200-foot-tall ferris wheel against the spectacular views of Lake Michigan and the Chicago skyline at this 50-acre scenic waterfront stretching out into Lake Michigan. Or just sit and enjoy the spectacular breeze on this pier full of restaurants and shops.
Wrigley Field
Check out the legendary home of the Chicago Cubs anytime, take a tour, or experience a baseball game on Memorial Day (Colorado Rockies at Chicago Cubs - 1:20pm). Take the Red line "L" train to Addison!
Murphy's Bleachers
Craft beer, great pub food, and baseball everywhere in this huge space right across from Wrigley Field. Take the Red line "L" train to Addison!
The Second City
Bill Murray, Stephen Colbert, Tina Fey, Eugene Levy, Mike Myers, and Martin Short are just a few of the famous names from this theater devoted to sketch and improvised comedy. With so many different shows to choose from and a super fun atmosphere, you’ll see some of the most talented rising comedic talents and future Saturday Night Live cast members.
Chicago Symphony Orchestra
Check out the Chicago Symphony Orchestra for a night of beautiful music, and keep your eye out for Cassiel's college violin professor - Blair Milton!