Are you or your #1 pal getting married this summer? Come celebrate your bachelor/ette party in Chicago! Don’t worry about trying to comb through the city’s endless options for the best hotels, restaurants, and activities; the expert Chicagoans at Bobby’s Bike Hike have got you covered.

Step One: Check-In

Moxy Hotel Chicago 

This funky boutique hotel, located in the heart of River North, is perfect for groups of pals like to get made up and have a good time! The lobby bar serves up amazing cocktails and fresh gourmet tacos, and regularly hosts drag shows and fashion industry events.

Hotel Lincoln 

This landmark spot just north of the Loop is perfect for the creative set, and those with a sense of humor. The Hotel Lincoln is known for its legendary “Gallery of Bad Art.” Furthermore, the rooftop bar, The J. Parker, is named for the bodyguard who was on duty the night Lincoln was assassinated. That’s some tongue-in-cheek humor to the nth degree.

The Viceroy 

Located right where State Street meets Rush Street in the Gold Coast neighborhood, this hotel is a stunning symbol of the high life with a modern flair. The Viceroy is the perfect choice for the shop-til-we-droppers because of its proximity to the Gold Coast’s legendary shopping.

Ace Hotel 

Foodies, book here! The trendy Ace Hotel is located in the center of the Fulton Market District, also known as the West Loop. The West Loop is home to some of Chicago’s most innovative and award-winning restaurants and bars, including one on the Ace Hotel’s very rooftop.

Step Two: Relax

Aire Ancient Baths 

These unique and totally serene pools and spas are by far the most relaxed you can get in the downtown area. You will be transported to a Roman citadel or perhaps the Little Mermaid’s grotto when you step inside Aire’s doors.

Piva Beer Spa 

Do you and your crew love beer? Do you also love to relax? Combine the two at Piva Beer Spa, where you can get a beer mask on your face and soak in a giant vat of hoppy goodness, all in the name of wellness!

Cowshed Spa at Soho House 

This spa is perfect for the laid back crew. It’s neo-rustic vibe (farmhouse chic) will put you right at ease and take you back to laid back days without the hustle and bustle of city life.


Step Three: Chow


This restaurant, located on the ground floor of the Viceroy Hotel, makes its owns breads and pastas from scratch. The service is unmatched and the atmosphere is celebratory.

Duck Duck Goat 

This is the Chinese restaurant owned by famous Chicago chef, Stephanie Izard (the girl behind The Girl and the Goat). The flavors are complex and authentic, and the menu extensive. You’re sure to find something to wow every member of the squad.

Lakefront Restaurant 

Our friends over at Lakefront Restaurant (inside the events and performing arts venue known as Theatre on the Lake) are cooking up some of the tastiest new American food in the city, all with a panoramic view of the skyline and Lake Michigan.

Nico Osteria 

This is a local favorite Italian restaurant with an emphasis on seafood, handmade pasta, and fine wine. The team behind Nico has produced some of Chicago’s all-time favorite restaurants including The Publican and Big Star, so the quality experience is a given.

Leña Brava 

This is the Baja-inspired upscale seafood restaurant by chef Rick Bayless, famous for his show, Mexico: One Plate at a Time. It also boasts the largest collection of mezcal in the city, so get ready for some smoked agave-fueled fun.


Step Four: Explore

Bikes, Bites, & Brews – Signature Edition

This is Bobby’s Bike Hike’s most popular tour, and we understand why: it combines the fun and relaxation of city biking with deep-dish pizza, Chicago-style hot dogs, and craft beer. It’s perfect for solo travelers, but it’s also an amazing experience for bachelor/ette parties looking to do something more active for their celebration.

Chicago River or Lake Michigan Boat Cruise 

There are a wide array of companies offering to take you and your group out on the water during your visit to Chicago. You could do an architecture river tour, or a high-speed journey on the lake, or a dinner and dancing cruise that explores both.


At the top of 875 N. Michigan Avenue, better known as the John Hancock Center, there is an observation deck that recently debuted one of Chicago’s craziest thrill attractions: Tilt! Up on the deck, you will stand in front of a glass window that will slowly tilt you out to a 45-degree angle over the city and lake below. Perfect for the parties that are looking to get really crazy!


Step Five: Party On


If you’ve ever seen a tugboat shaped building sitting on one of Chicago’s most popular beaches, then you’ve already spotted Castaways. This legendary snack shack and bar is the perfect place for summertime partying. A trip to North Avenue Beach just isn’t complete without stopping at Castaways.

Three Dots and a Dash 

In the heart of the River North nightlife scene, there’s a tiki bar with a secret entrance and a long list of fruity, rum-based cocktails just waiting for you and your friends to enjoy.

City Winery on the River 

The Chicago Riverwalk has become one of the most popular hangouts for locals and visitors alike. City Winery is easily one of the most frequented spots within. Kick it with your pals and sip award-winning wine while watching the boats go by.

Need more ideas?

Give us a call anytime at (312) 245-9300 and one of our expert guides can offer advice, or book a Chicago Tour online.