The Magnificent Mile: Must-Do Stops On Chicago’s Glamorous Strip

Going to Chicago and wondering about The Magnificent Mile. I’ve got you covered.

I still remember the first time I strolled down The Magnificent Mile.

Lined with iconic architecture, historic landmarks, drool-worthy restaurants, and some of the best shops in the Midwest, the Mag Mile is a must for anyone spending time in the Windy City.

Here’s everything I’d recommend doing, eating, and exploring along the Magnificent Mile Chicago plus a few tips just to help you make the most of your stay.

Where Is The Magnificent Mile?

The Magnificent Mile is a lively section of Michigan Avenue in Chicago, stretching from the Chicago River up to Oak Street.

It’s flanked by River North to the west, Streeterville to the east, and Lake Michigan just a few blocks away.

It’s walkable, scenic, and packed with everything from department stores to historic gems like the Chicago Water Tower, one of the few buildings to survive the Great Chicago Fire.

If you are traveling to Chicago for the first time, please read my tips.

Shopping On The Magnificent Mile

To most, including me, Magnificent Mile shopping is the main event for a lot of visitors.

From luxurious flagship stores to cosy boutiques, there’s something for every style and budget.

One of the most iconic shopping spots is Water Tower Place, a multi-level indoor shopping mall that features everything from Macy’s and American Girl Place to Sephora and Akira.

Just a short walk north, 900 North Michigan Shops offers a more upscale experience with Bloomingdale’s, designer boutiques, and sleek little cafes that make great pit stops.

If you’re into department stores, don’t miss Nordstrom or Neiman Marcus.

Tech lovers and sneaker lovers won’t want to skip the Apple Store and Nike Chicago, they are amazing stores.

People-watching here is practically a sport, and the window displays are out of this world.

Read my suggestions on the best boat tours in Chicago. (I highly suggest taking an architectural boat tour!)

Magnificent Mile Restaurants You’ll Love

Need a break from all the shopping? The Magnificent Mile restaurant scene is every bit as impressive.

I love The Purple Pig. Their Mediterranean-inspired menu is full of wonderful small plates, their wine list is divine, and the outdoor patio is perfect on a sunny day.

Just off the Mile, Eataly Chicago is a foodie’s dream come true. Think fresh pasta, Italian wine, espresso bars, and even groceries to take home.

When I want something quick but comforting, I head to Labriola Bakery & Cafe. It’s one of those spots that does deep-dish pizza as well as dreamy desserts.

If you’re aiming for a sky-high view to match your meal, the Signature Room at the 95th, while technically just off Michigan Avenue, is unbeatable. Sunset views and cocktails? Yes, please.

If you are deep into shopping, there are plenty of fast food options like Chipotle.

If you love food how about The Ultimate Foodie Walking Tour with Tasty Stops?

Can’t-Miss Magnificent Mile Attractions

There’s more to do on the Magnificent Mile Chicago than just shop and eat. It’s also home to some of the city’s most iconic attractions.

You can start with the historic Chicago Water Tower, built in 1869, and one of the only buildings to survive the Great Chicago Fire.

It is one of the most photographed spots in the city. When you see it, you will know why.

Next, walk a bit further and stop at the Tribune Tower.

Its Gothic architecture is stunning, but what makes it truly unique are the real stones from global landmarks embedded in its exterior. There are stones from the Great Wall of China to the Berlin Wall.

If you’re in the mood for art, the Museum of Contemporary Art is just a few blocks away and perfect for a quiet, creative detour.

It is one of the best museums in Chicago.

For jaw-dropping views, nothing beats the 360 Chicago Observation Deck, located at the top of the former John Hancock Center.

Be brave and try “TILT,” a glass enclosure that tilts you outward from the 94th floor. It’s scarier than it sounds, and so worth it.

Pre-book your 360 Chicago Observation Deck Sip and View Ticket.

Hidden Gems Just Off The Magnificent Mile

If you have a little extra time, some of the best surprises are tucked just around the corners of the Mag Mile.

One of my favourite discoveries is P.O.S.H. Chicago, a treasure trove of vintage-inspired French homeware and quirky travel curiosities. I

Another hidden gem is the Driehaus Museum, located in a beautifully preserved Gilded Age mansion.

If you’re craving a bit of peace, step into the grounds of Fourth Presbyterian Church.

Take a Lake and River Architecture Cruise to see more of the sights.

The Magnificent Mile: Where To Rest Your Feet

There are plenty of relaxing places to recharge.

Café Crèmerie is my go-to for a quick escape. Tucked away and beautifully styled, it feels more European than Midwestern.

Many of the hotel lobbies in the area make for great resting spots too.

If you’re visiting in summer, grab a rooftop drink at Z Bar or LondonHouse Rooftop for sweeping skyline views.

Here are some great rooftop bars in Chicago if you are looking for more.

Magnificent Mile: A Walking Itinerary.

Start your morning at Café Crèmerie or Intelligentsia Coffee with something warm and a pastry.

Then head north to explore Water Tower Place or pop into Nordstrom if you’re short on time.

Mid-morning is perfect for visiting the Museum of Contemporary Art or admiring the Chicago Water Tower before the crowds hit.

For lunch, stroll to The Purple Pig and share a few small plates, or head to Eataly if you’re craving carbs.

Spend the afternoon browsing shops at 900 North Michigan or just enjoying the sights and sounds of Michigan Avenue Chicago.

Before sunset, make your way to 360 Chicago and brave the TILT.

Then, celebrate your day with a cocktail and skyline view from the Signature Room or Z Bar.

End with a quiet walk past the twinkling lights and a promise to return soon.

Read my suggestions on the tours in Chicago you should consider.

Traveling to Chicago: Essentials Packing List

If you will be traveling to Chicago by plane or car, here are some tips on how to pack lightly.

This unisex RFID-blocking concealed travel pouch is lightweight and comes in several colors.

These RFID sleeves are another solution.

This Anker high-speed phone charging battery is the exact one I carry with me on all of my trips.

My daughter gifted me this FugeTek selfie stick and tripod setup for my birthday. It is made of lightweight aluminum and is so easy to use.

I never leave home on a trip without my Bobble filtration bottle. The 18.5-ounce size is perfect for exploring.

And the replacement carbon filter ensures fresh, clean water whenever you fill the Bobble.

Then this collapsible silicone foldable water bottle would work well for you as well.

This foldable water-resistant backpack would be great for a daily go-pack.

These quick-dry slip-on Aqua shoes will be useful when heading to Chicago’s beaches.

These men’s quick-dry trunks are essential.

For women, this one-strap one-piece bathing suit is amazing.

Consider bringing along quick-dry super-absorbent microfiber towels.

This wet-dry bag with handles is a good option.

These unisex polarized sunglasses come in many lens colors and frame designs and are extremely affordable, too.

If you like aviator-style sunglasses, these polarized aviators may interest you.

As an Amazon Affiliate, I earn from your qualifying purchases.

The Magnificent Mile: Events, Lights, And Seasonal Magic

If you’re visiting during winter, don’t miss the Magnificent Mile Lights Festival.

It’s a beloved holiday tradition that kicks off the festive season with a parade, a tree lighting ceremony, and plenty of twinkle lights to go around.

There’s nothing quite like it; it feels like a winter wonderland.

The Magnificent Mile: Hotels

Mag Mile hotels range from ultra-luxe to surprisingly affordable, depending on what you’re after.

If you want the royal treatment, The Peninsula Chicago is your go-to.

It’s elegant, quiet, and the service is impeccable. The rooms feel like a sanctuary, and the rooftop spa is next-level.

For something more playful and modern, check out Hotel EMC2, Autograph Collection. It’s full of quirky touches, artistic flair, and even has robot room service!

Historic hotel lovers will adore the Warwick Allerton, which oozes vintage Chicago charm while still being right in the thick of things.

And if you’re looking for a clean, stylish base with great value, AC Hotel by Marriott ticks all the boxes.

Quick Tips For Visiting The Mag Mile

The Magnificent Mile is beautiful, but it’s a lot of walking. Stylish sneakers or city-friendly boots are your best friend.

Pack a crossbody bag, bring a reusable water bottle, and if you plan to shop, leave a little extra room in your suitcase.

I’ve always felt comfortable walking alone here, even in the evenings.

It’s well-lit and bustling, but as always, stick to main streets and trust your instincts.