Once an industrial district, West Loop is now one of Chicago’s hottest neighborhoods, known for its incredible dining scene and trendy vibes.

Au Cheval – Home to what’s often called the best burger in America.

Fulton Market Street – Walk around and soak in the industrial-chic atmosphere, with tons of cool restaurants and rooftop bars.

Guinness Open Gate Brewery - This is Guinness’ only U.S. brewery outside of Baltimore. It offers a mix of classic Irish stouts and new experimental brews crafted just for Chicago. The space is massive, featuring a beer garden, taproom, and restaurant serving elevated pub fare.

Trivoli Tavern - One of the Lauren's favorite restaurants!! Tucked down a cobblestone alley, this candlelit tavern serves upscale American and European-inspired dishes alongside craft cocktails and an extensive whiskey selection.

Lyra – Another one of Lauren's favorite restaurants!! A modern Greek restaurant with a stunning open-flame kitchen, Mediterranean-inspired cocktails, and a lively atmosphere.

Walk Down Wells Street – The heart of Old Town, Wells Street is lined with unique boutiques, coffee shops, bars, and restaurants. It’s a great place for a leisurely stroll, shopping, or people-watching.

The Second City – Catch a comedy show at the legendary improv theater where stars like Tina Fey, Bill Murray, and Steve Carell got their start.

Twin Anchor's – Lauren and Joey's favorite place to catch a quick dinner or order some takeout. A historic gem in Chicago’s Old Town known for its legendary ribs and classic charm, it’s an ideal spot for a fun and memorable gathering.

Old Town Ale House – One of Lauren and Joey's favorite bars!! A dive bar with tons of character, quirky artwork, and a history of being a late-night favorite among comedians and locals. CASH ONLY!

Armitage Ale House – A cozy, old-world-style tavern with dark wood interiors, vintage decor, and an incredible menu of elevated pub fare and craft cocktails.

Lincoln Park Zoo – One of the country’s oldest free zoos, this is a must-visit for animal lovers and families. The scenic park setting makes it a great place for a walk, even if you’re just passing through.

Green City Market – A fantastic farmers’ market (April–November) offering fresh produce, baked goods, and local eats right in Lincoln Park.

The J. Parker Rooftop – A rooftop bar with stunning views of the park and Lake Michigan, perfect for sunset cocktails.

Cafe Ba-Ba-Reeba! – A staple in Lincoln Park for delicious Spanish tapas and sangria, great for group dining.

Gibsons Bar & Steakhouse – A Chicago institution, perfect for a steak and a classic dirty martini. Great for people-watching, especially on the patio. Another one of Lauren and Joey's favorite bars!!

Maple & Ash – A modern, high-energy steakhouse with amazing cocktails and a fun, lively atmosphere.

LuxBar – A stylish yet relaxed spot for cocktails, burgers, and brunch.

Le Colonial – A beautiful French-Vietnamese restaurant with a romantic, Parisian-style atmosphere.

The 3 Arts Club Café (inside RH Chicago) – A stunning café inside Restoration Hardware, featuring chandeliers, indoor trees, and a serene courtyard. Perfect for a coffee, brunch, or glass of wine.

Oak Street Shopping District – Chicago’s version of Rodeo Drive, featuring high-end designers like Hermès, Prada, Chanel, and Saint Laurent.

The Riverwalk – Stroll along the Chicago River, grab a drink at a riverside bar, and enjoy the views.

Architecture River Cruise – One of the best ways to see Chicago’s iconic skyline and learn about its history.

Skydeck at Sears Tower – Stand on The Ledge, a glass box that extends 1,353 feet over the city.

Millennium Park & The Bean – Take the classic Chicago tourist photo and explore the park.

Lakefront Trail – Rent a bike or go for a walk along Lake Michigan with amazing skyline views. Oak Street Beach is across from The Drake and will have a Divvy Bike rack for renting.