Your High-End Shopping District in Downtown Chicago

In the heart of downtown Chicago, the Oak Street District is the city’s destination for luxury shopping. A neighborhood of historical buildings housing the world’s most sought-after brand names and designers, it is a mélange of both charm and culture. Located only steps away from Michigan Avenue, the Oak Street District continues to draw in millions of visitors each year with walkways that act as red carpets to posh storefronts and inspired interiors. It is the gem of Chicago’s Gold Coast, one of the most prestigious regions in the Midwest and the second wealthiest neighborhood in the nation.

Looking for a Reliable Local Business Directory?

Welcome to the most thorough local business directory in the downtown Chicago area! Let us help you find what you are looking for, from the best restaurants and fine dining establishments to the best spas, hotels, and accommodations. Our local business directory is here to assist you in finding the best Chicago has to offer.


Discover your new home away from home. Our directory includes an expansive list of top-notch boutique and big-name hotels. Each is designed to make you feel like royalty.


Home of the James Beard Awards, Chicago prides itself on having some of the world’s best chefs and most innovative restaurants. The Oak Street District is home to the area’s most talked about culinary masters, and not to be overlooked are our popular lounges and bars, famous among locals. Choose your cuisine from our comprehensive listing of dining choices.


Ready for a shopping experience like no other? Our listing includes a vast array of designer clothing stores, couture jewelry and timepieces, fine footwear, and ready-to-wear boutiques. We’ve listed every possible option for the best shopping in the city!

Experience Chicago As Never Before

For the best shopping, boutiques, fine dining and luxury lifestyle services for living in Chicago, Oak Street Chicago takes the cream of the crop from the downtown Chicago area and puts it on the front page.

We’ll help navigate downtown Chicago, so you can stroll confidently into the best restaurants, hotels, hostels, accommodations and clothing boutiques the city has to offer. Browse Oak Street Chicago’s local business directory for a thorough catalogue of boutique shopping, and restaurants and you’ll know exactly what to select on your destination adventure.

Browse and Become a Local

With Oak Street Chicago, you can go deeper than online reviews. Our guide offers an inside look at the mélange of both charm and culture of the shops, restaurants and fine dining in Chicago. With a curated list of destinations, we can guide you from start to finish through each of Chicago’s tree-lined and skyscraper studded neighborhoods. Get an inside look through the glass panes of our directory today to save you time plodding the pavement when you’re outside the shops on the weekend.

A Catalogue at Your Fingertips

Our local business directory acts as a tour guide to Chicago’s premiere destinations. Peek into the shopping, cuisine and best hotels in Chicago and browse our section on events to plan your schedule out perfectly. Whether it’s the best spas, hotels, accommodations, restaurants or a shopping district in Chicago, Oak Street Chicago lets you find what you’re looking for. You’ll explore the luxury lifestyle boutiques Chicago’s downtown district shines for and discover Chicago’s finest attractions the casual tourist overlooks.

Cuisine and Luxury Shopping in the Heart of Downtown

If you’re stepping out for fashion, food or fun, we can assist you on your search for high end shopping destinations. Oak Street Chicago shows you the best in designer and couture, culinary and culture in the Windy City. Millions stream into downtown district every year and indulge on designer brands, chef-inspired dishes, and world-renowned playhouses and comedy shows. See what boutique shopping in Downtown Chicago has to offer, which shops offer the brands you want and why locals love to visit them.

Discover Your Favorite Shopping District

The most delectable gelaterias, Italian designer boutiques, dream luxury spas with rooftop views and hidden gems of the city aren’t spots you want to pass over on your visit to Chicago’s Downtown district. We’ve listed the world’s top creators of fine jewelry, couture clothing and sought-after fashion houses in the downtown area. Find your preferred shopping district in Chicago with our guide that lists the shops in each area and makes your trip more than worth its while.

See a Show, Follow a Wine Stroll or Enter a Designer Giveaway

Plan on going out? Oak Street Chicago also lists the latest luxury events in Downtown Chicago. From wine strolls to weekend bashes with designer giveaways, Chicago’s latest happenings are all available on our events page. Read on the Oak Street Chicago blog for shopping tips, fashion insights, and luxury trends in Chicago’s premiere luxury destination.

The Best Chicago Has to Offer



Chicago's Most Popular Culinary Scene

Dine at the city’s most popular restaurants!


Designer and Couture

The world’s top creators of fine jewelry, couture clothing, and sought-after fashion houses!


The center of Nightlife and Leisure

From happy hour to Saturday night, there’s no better place to be then on Oak Street!

See what’s new!

Keep up with District Events

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