Prepare to be awed as the Chicago River cuts through the heart of downtown like a canyon, surrounded by the tall, iconic buildings that define Chicago’s landmark skyline. Consider booking an architectural boat tour to learn about the famous buildings you'll see while cruising down the river. Or, for more adventure, kayak through the river yourself at one of the rental booths (fair warning: you do share the river with the big boats!)
See the views from the heart of Chicago's "Loop" downtown and visit the iconic Bean. Head up to Cindy's Rooftop for a drink and a view of the whole park. If you're up for a longer walk, you can walk further down south past the Art Institute and into Grant Park to see Buckingham fountain. Sightsee like high school Linda who thought she was a cool suburbanite taking the train into the city to take photos with her friends...
If you make it out of bed on Sunday, buy a ticket to see the Cubs play at Wrigley Field (https://www.mlb.com/cubs/tickets/single-game-tickets)
Visit, in our opinion, the best art museum in the country. See famous Impressionist paintings like Georges Seurat's A Sunday Afternoon (painted entirely with dots!) to American classics like the American Gothic couple and Edward Hopper's Nighthawks (Linda's favorite). Plus, head down to the basement for the Thorne Miniature Rooms, another childhood favorite of Linda's.
Yes, if you didn't know - Chicago does have beaches, many in fact! Enjoy some freshwater swimming in Lake Michigan. The water is very clean and comfortable, though it may still be a little cold in June (peak season is July/August when the water is the warmest). Other popular beaches include Oak Street Beach and North Avenue Beach. You can also head up to Montrose Beach in Uptown for a quiet, less touristy beach. For any beach, we do recommend you uber - it can be very hard to find parking!
One of our favorite things to do - and a great way to explore Chicago's scenery - is by bike! Start north on the trail from Lincoln Park and see the transition from park to skyline all while having the lake and beaches on the other side. Pass the lakefront buildings of the Gold Coast and Streeterville neighborhoods, bike past Navy Pier, go over the bridge over the Chicago River in the loop, bike along Millennium Park and Grant Park, and enter the South Loop museum campus where you can get impressive skyline views from the Shedd Aquarium and the Adler Planetarium. You can go even further south and reach our wedding venue, Promontory Point!
We'll be having some of our wedding weekend activities in this neighborhood, also known for having some of Chicago's best restaurants and bars. Highly recommend the Girl & the Goat for creative New American dishes, Au Cheval for their amazing burger, and Trivoli Tavern for an old world vibe down a cobblestone alley. For drinks, grab cocktails at Bisous, Fox bar (inside Soho House), or Lazy Bird. They do get busy on weekend nights though!
Linda grew up going to this Chinatown. Visit the Chinatown Square Plaza (new Chinatown) or the strip down Wenworth Ave (older Chinatown) for authentic Chinese food. You can uber, take the CTA Red Line, or even the water taxi from downtown! Our faves include Ken Kee (Cantonese/Hong Kong food), MingHin (amazing dimsum), Happy Lamb (for hotpot), MCCB (for Sichuan) and B.B.Q. King (to grab a platter of roast duck or BBQ pork - yum!) And if you need to walk off the food after, take a stroll through Ping Tom Memorial Park along the river.
We're hardcore deep dish lovers and celebrated relationship milestones early on by shipping Lou Malnati's to where we lived in California. You can't go wrong with ordering the Malnati Chicago Classic pizza.
Visit one of Chicago's most trendy, hipster neighborhoods. Get off on the CTA's Damen stop on the blue line and explore Milwaukee Avenue for artisan coffee shops (recommend The Wormhole Coffee), book stores (Myopic Books), and vintage shopping. From this neighborhood, it's also easy to enter the Bloomingdale Trail, also known as the 606, a former rail line and elevated scenic trail inspired by NYC's High Line. Walk or bike through this elevated park to see Chicago's charming Northwest neighborhoods from above.
Visit this free, city zoo inside Chicago's main park on the Northside. You also get a great skyline view of downtown.
If you have time to go uptown – ridiculously good birria that Linda was compelled to write a Google review about (when she never does).