Ashley & James
Things To Do
Chicago Architecture Boat Tour
Explore Chicago's rich architectural history by taking a boat tour along the Chicago River. You'll learn about the city's most famous skyscrapers and historic landmarks from the water - it's a must-do experience for architecture lovers!
Chicago Breweries
Chicago is home to a vibrant craft beer scene, with breweries ranging from small, local spots to renowned favorites. If you love beer, take some time to explore these top Chicago breweries during your visit: Revolution Brewing: One of Chicago's largest craft breweries and a local favorite. Known for their flagship beers like Anti-Hero IPA and seasonal brews, it's a must-visit for beer lovers. Goose Island Beer Co.: One of the most well-known Chicago breweries and has been a staple in the city's beer scene since 1988. Famous for their Bourbon County Stout and 312 Urban Wheat Ale. Half Acre Beer Company: Half Acre offer a range of hoppy and balanced beers, with their Daisy Cutter Pale Ale being one of the most popular local brews. Metropolitan Brewing: Located on the Chicago River, Metropolitan Brewing focuses on traditional German-style lagers. Their spacious taproom offers a relaxing spot to enjoy beers with views of the river.
Chicago Food
Chicago is a city known for its iconic eats, and no trip is complete without trying these local favorites: Deep-Dish Pizza: This hearty, cheese-loaded, thick-crust pizza is a must. Head to Lou Malnati's, Giordano's or Pequod's (James' choice) for the best slices. Just be prepared to wait, as deep dish takes time. Italian Beef Sandwiches: Thinly sliced roast beef on a roll, often dipped in savory juices and topped with peppers or giardiniera. This messy delight should be tried at Portillo's (Ashley and James' choice), Al's Beef, or Johnnie's Beef. Chicago-Style Hot Dogs: An all-beef dog topped with mustard, relish, onions, tomatoes, pickles, sport peppers, and celery salt - never ketchup! Grab one at Portillo's (James and Ashley's choice), Superdawg, or Gene & Jude's.
Chicago Riverwalk
Take a scenic stroll along the Chicago Riverwalk, offering some of the best views of the city's stunning architecture. Grab a coffee or stop for a bite at one of the many riverside restaurants.
Lincoln Park Zoo
The Lincoln Park Zoo is one of the oldest zoos in the U.S. and is free to the public. Take a walk around and see everything from lions to penguins, and enjoy the surrounding Lincoln Park neighborhood.
Magnificent Mile
For those who love shopping, the Magnificent Mile is a must-see. This stretch of Michigan Avenue is home to world-class shops, luxury boutiques, and great dining options. Be sure to check out Water Tower Place and the historic Wrigley Building.
Millennium Park & The Bean
No trip to Chicago is complete without visiting Millennium Park to see the iconic "Cloud Gate" sculpture, more famously known as "The Bean". Wander through the park, check out the nearby Crown Fountain, or relax by the Lurie Garden.
Navy Pier
Navy Pier offers entertainment for all ages, from amusement rides to boat tours along Lake Michigan. Stroll along the pier, or take a spin on the Centennial Wheel for stunning views of the skyline.
Shedd Aquarium
Dive into the aquatic wonders of Shedd Aquarium, home to over 32,000 animals from the world's oceans, rivers, and lakes. Don't miss the live animal presentations and 4D experiences.
The Art Institute of Chicago
Art lovers, don't miss the chance to visit one of the largest and most prestigious art museums in the world. The Art Institute is home to famous works like "American Gothic" and "A Sunday on La Grande Jatte".
The Second City
Comedy lovers, don't miss a visit to The Second City, the world-famous comedy theater known for launching the careers of countless comedic legends like Chris Farley, Tina Fey, Steve Carell, and Bill Murray. Whether you are a fan of improv, sketch comedy, or stand-up, The Second City is the perfect spot for a night of laughter and entertainment.
Willis Tower Skydeck
If you're not afraid of heights, take a trip to the Skydeck on the 103rd floor of the Willis Tower (formerly Sears Tower) and step out onto "The Ledge" - a glass box that extends outside the building!
Wrigley Field
If the Cubs are in town, catching a Cubs game at Wrigley Field is an unforgettable experience. The energy of the crowd and the sight of the ivy-covered outfield walls make it a classic Chicago activity. Before and/or after the game, walk Wrigleyville and visit fan-favorite spots like Murphy's Bleachers, Sluggers, and The Cubby Bear.