Jaclyn & Jacob
Things To Do
Chicago Riverwalk
The Chicago Riverwalk is located downtown and stretches 1.25 miles from Lake Michigan to Lake Street. Along the way you’ll see intimate coves, breezy cafes, wineries and bars, public art, monuments, museums, and a boatload of excursions on the water. There are many places to access the Riverwalk. Check out the link if you're interested.
Chicago River Boat Architecture Tours
Experience the city’s legendary architecture from the best seat in the house—the river. The tour navigates through the heart of the city on all three branches of the Chicago River. This is a great way too see and explore downtown Chicago!
Millennium Park
Millennium Park is a staple Chicago attraction. The lakefront campus, located in the heart of downtown, is home to the iconic Cloud Gate statue (aka “The Bean”), interactive fountains, tranquil gardens, public art, rock climbing, and plenty of green space. For more information about Millennium Park and how to access it, check out the link here.
The Art Institute of Chicago
Located downtown by Millennium Park, the Art Institute of Chicago is one of the oldest and largest museums in the country, housing an extraordinary collection of objects from across places, cultures, and time. It was voted by Tripadvisor as one of the “Best of the Best” US attractions in 2024 and the only museum in the world to be top ranked four years in a row.
The Second City
The Second City is a classic Chicago comedy experience. Its productions mix sketch and improv, delivering sharp satire, spontaneous laughs, and a unique experience each time. Productions include the mainstage improv show (which is always excellent), as well as other stand-up acts and sketch comedies. Famous actors who began their careers or have appeared at The Second City include Stephen Colbert, Tina Fey, Amy Poehler, and many more. It is a 10-15 minute drive from the suggested hotels. We strongly suggest booking in advance if you're interested.
Lincoln Park Zoo
Lincoln Park Zoo is one of the oldest and most modern zoos in the country. It is also one of the few zoos with free admission. The zoo is home to 200 unique animal species and immerses you in its beautiful gardens, which include more than 850 plant species. It is a 10-15 minute drive from the suggested hotels.
Shedd Aquarium
Shedd Aquarium is a highly-ranked aquarium and one of the largest indoor facilities in the world. The aquarium is located along Lake Michigan in the city's Museum Campus, which also includes other highly-ranked institutions such as Adler Planetarium and the Field Museum of Natural History. It is a 10-15 minute drive from the suggested hotels.
Beatrix
Beatrix is a neighborhood restaurant and coffeehouse located in Fulton Market, within walking distance from the suggested hotels. It also has locations in various other Chicago neighborhoods including River North, Streeterville, and Oak Brook. It is a cozy, trendy spot that serves breakfast, lunch, and dinner and combines an American cafe and bakery, with a wine and cocktail bar.
The Loyalist
Inspired by neighborhood French restaurants, The Loyalist features casual fare with the same uncompromising attention to detail and love as Smyth, its fancier 3 Michelin-starred restaurant sibling upstairs. Located in the West Loop, within walking distance from the suggested hotels. If you're trying to get into Smyth, book WELL in advance.
Aba Restaurant
Aba is a Mediterranean restaurant with California influence located in Fulton Market, a short walk away from the suggested hotels. Its rooftop patio has a magnificent city view and provides a cozy atmosphere with lots of lighting and beautiful greenery. This is a very popular spot so we suggest booking reservations in advance if interested.
Green Street Smoked Meats
Green Street Smoked Meats is located down a charming brick paved alleyway in Chicago's West Loop neighborhood, within walking distance from the suggested hotels. It is a nationally acclaimed restaurant that beckons guests with rock music and house smoked, Central Texas-inspired BBQ served at the counter in a warehouse-style restaurant.
Lone Wolf Tavern
Neighborhood tavern with an old-school, divey vibe offering craft beers, classic cocktails, and bar bites. A solid late-night spot in the West Loop, within walking distance from the suggested hotels.
Haymarket Pub & Brewery
Rustic brewpub offering a rotating selection of house brews & pub food, plus occasional live music. Located in the West Loop, within walking distance from the suggested hotels.
Randolph Street
Randolph Street is the main street that runs through the West Loop neighborhood. Its attractions include its many retail shops and dining spots, all within walking distance from the suggested hotels. For clothes shopping, there's Anthropologie, Allbirds, Madewell, Notre, Lululemon, and Free People (to name a few). Cosmetic shops include Scratch Goods and Bluemercury. There's also plenty of trendy boutiques. For restaurant ideas, see some of our other suggestions throughout this list!
Magnificent Mile
The Magnificent Mile is one of the most iconic shopping areas in the world. This cosmopolitan strip, located downtown on Michigan Avenue, leads you from department stores to multistory retail centers to luxury boutiques to brand-name retail chains — all within walking distance. For a guide to all the various shopping options, including a link here.
Block 37
Block 37 is a hip & urban shopping, dining and entertainment destination, within a five-story atrium that is spread out over an entire block in the heart of Chicago's Loop. It is a 5-10 minute drive from the suggested hotels.