Chicago: My Favorite Spot for Shopping & Afternoon Tea

The location of The Peninsula really can’t be beat. You are steps from Oak Street and right off Michigan Avenue, which makes shopping incredibly easy. While there isn’t shopping directly inside the hotel, everything is right there, from 900 North Michigan Shops to The Shops at North Bridge and Water Tower Place. You can go out for a few hours, pop back to the hotel to reset, and head right back out again.

The rooms are classic Peninsula—spacious, quiet, and really well done. You can choose from deluxe rooms, suites, and larger suite options, depending on how much space you want, and everything feels elevated but comfortable.

The pool is one of those hidden gems. It’s indoors with floor-to-ceiling windows overlooking the city, so it feels bright and relaxing year-round. It’s calm, never chaotic, and such a nice reset after being out in the city.

Dining here is such a highlight and part of the whole experience. Breakfast is included when you book through me, which is a huge perk, and something you definitely want to take advantage of. Sitting in the lobby for breakfast or afternoon tea is one of my favorite parts of the stay. It’s light, beautiful, and just feels special without trying too hard. For breakfast, go classic—eggs, pastries—and really take your time.

Afternoon tea is a full experience here, and, during the holidays, their holiday tea is something you absolutely need to book ahead of time because it sells out. It’s festive, elegant, and just feels like Chicago during the holidays.

The hotel has great dining options throughout. Shanghai Terrace is perfect for a more elevated dinner, and Pierrot Gourmet is great for coffee, pastries, or a quick bite.

Upstairs at Z Bar is always a fun spot, but during the holidays it becomes a full experience. It turns into a festive bar with seasonal cocktails, cozy decor, and such a fun atmosphere. It’s the perfect place to end the night.

Right nearby at 900 North Michigan Shops is Merchant & Rhoades, a barbershop that’s always busy and definitely a favorite for the guys. It’s such an easy add-on while you’re in the area and feels like one of those little Chicago finds.

The spa is another standout. It’s such a peaceful escape in the middle of the city, and they offer seasonal treatments that feel really unique, especially during the holidays.

And during the holidays, this hotel becomes truly magical. When I checked in, I turned the corner and Santa and Mrs. Claus were standing there—it just set the tone for the entire stay. They also have an ice-skating rink and a gingerbread house where you can go in, grab a bag, and fill it with candy. It sounds like it’s for kids, but honestly, even as an adult, it felt so fun and festive.

It's always exciting walking off the elevator to see what the lobby decorations will look like.

They are also incredibly family-friendly. From children’s robes and slippers to scavenger hunts, in-room tents, games, and even visits from their Pen Bear mascot, they really go out of their way to make it special for kids while still keeping that luxury feel for adults.

Outside of the hotel, there’s so much to do. Walking along the Chicago Riverwalk is always one of my favorite things to do, especially watching all the boats go by. You can grab lunch or dinner right along the water, and one of the most popular spots there is RPM Seafood. I’ve even seen live bands along the river, which makes it such a fun place to spend time, and kayaking through there is always a fun way to see the city from a different angle.

Heading over to Navy Pier is always fun, whether it’s for lunch, dinner, or just walking around. You can take a speedboat ride from there and see the city from the water, which is such a cool perspective.

If you’re there in the summer, the city really comes alive. There are so many events happening, and it’s just a fun time to be there. I’ve even seen Mick Jagger at Soldier Field, which just shows you never know what kind of moment you’re going to have in this city.

There are also great summer events like Windy City Smokeout, Lollapalooza, Taste of Chicago, and the Chicago Air and Water Show, along with major shows like the Auto Show and Boat Show at McCormick Place.

And you can’t come to Chicago without trying a few of the classics. Portillo’s is always a must for a Chicago-style hot dog or Italian beef, and grabbing a bag of Garrett Popcorn while walking around the city is just part of the experience.

For Italian, one of my favorites is La Scarola—it has that cozy, old-school Chicago feel and is always a great meal.

For steak, Gibsons Bar & Steakhouse is a must, especially sitting outside in the summer. The shrimp cocktail is huge, the wedge salad is a classic, and you really can’t go wrong with the prime rib or a filet.

If you’re looking for something with a view of Lake Michigan, spots like Cindy’s Rooftop, The Signature Room at the 95th, and Castaways all give you a completely different perspective of the lake and skyline.

And for something a little different, the Starbucks Reserve Roastery Chicago is more of an experience than just coffee.

Starbucks Reserve Roastery Chicago

If you love theater, the Chicago Theatre District is incredible, with everything from Broadway shows to smaller productions, and it’s such a fun way to spend an evening.

If you’re in town for sports, it’s always fun to catch a game. You’ve got the Chicago Bulls, Cubs, White Sox, Bears, and Blackhawks, so there’s always something happening.

For culture, the Art Institute of Chicago and Shedd Aquarium are great, and Lincoln Park Zoo is always a fun stop, too.

During the holidays, the Christkindlmarket Chicago is a must. Grab a mulled wine and bratwurst and just walk around—it’s such a fun experience. And of course, The Walnut Room is always a classic holiday stop.

And if you’re there in warmer months, catching a concert at Millennium Park is always such a fun way to spend an evening.

Millennium Park

One of my favorite little things is just walking the city and seeing how they decorate everything throughout the seasons; it just adds to the whole experience.

Chicago just has this energy—between the events, the lake, the food, and everything going on, it’s one of those cities that’s always worth going back to.

Booking through me adds that extra layer—breakfast included, potential upgrades, and added perks that just make the stay even better.

And in 2026, the hotel is celebrating 25 years in Chicago, which makes it an especially fun time to visit.

• Make afternoon tea reservations in advance, especially during the holidays, as it sells out.

• Plan shopping early in the day—Oak Street and Michigan Avenue get busy.

• Wear comfortable shoes—you’ll walk more than you think.

• Layer up—Chicago weather can change quickly, even in one day.

• If you want Riverwalk dining, go a little earlier to grab the best outdoor tables.

• Summer is perfect for outdoor dining and events, but fall and the holidays are truly magical.

• Leave time to just wander—some of the best moments are unplanned.

For more inspiration and insider recommendations, visit our Chicago page.