A Weekend in Chicago

Looking to spend a weekend in the Windy City? Look no further than my guide to a weekend in Chicago - with recommendations from where to stay, to the best restaurants, shopping, and a bit of culture along the way!

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A Weekend in Chicago

Growing up in Indianapolis, there's been no easier, nor more exciting weekend getaway than escaping to Chicago for the weekend! I can't count how many times I've been, and we were so happy to be able to return last year after a pandemic-induced hiatus. There's no one way to have a great trip to Chicago, but if you're only visiting for a weekend, I've rounded up a few of my itinerary suggestions!

Is a weekend enough time to see Chicago?

Drinks by the Chicago River - always a good decision

Of course a weekend isn't sufficient time to enjoy everything America's third largest city has to offer. But whether it's your first trip or your fiftieth, I can guarantee you'll find more than enough to keep you occupied anytime you visit Chicago.

When's the best time of year to visit Chicago?

Spring in Chicago (stock)

Well, obviously not winter. But aside from that, I've had wonderful trips to Chicago throughout the year. Be sure to check a city calendar, such as TimeOut, for major events that may make hotel room rate sky rocket (St. Patrick's Day, major conventions). If you're a big fest-goer, there is nearly always a fest to be had, or avoided, depending on your preference, in summer months.

Chicago Hotel Recommendations

Wondering where to stay during your weekend trip to Chicago? I've stayed a few places in my time, and I've narrowed down my Chicago hotel recommendations are below:

Viceroy Hotel Chicago's Gold Coast

Viceroy Chicago

For my money, you can't beat Viceroy Chicago in Chicago's Gold Coast neighborhood. A bit north of Michigan Avenue, you'd be surprised how quickly the tourists fall away. Featuring its own excellent dining options (and rooftop bar), a boutique feel, and unbeatable views, it's the perfect home base for a weekend getaway.

The Drake Hotel: Real Chicago

The Drake, Chicago

If you're looking to stay at a true Chicago legend, I can't recommend The Drake highly enough. Now owned by Hilton, The Drake isn't nearly as "stuffy" as it was years ago, but that's not to say it isn't enchanting. And if you're looking for an excellent way to spend an afternoon, don't forget about afternoon tea at The Drake!

A Weekend in Chicago

Assuming you've picked a place to stay, let's dive into a few of my favorite activities to fill my time during a weekend in Chicago, in no particular order:

Take a stroll along Lake Michigan

Strolling along the Lake

Pretend you're a local and take a stroll along Lake Michigan on a Saturday morning! There are a number of access points that allow you to use a tunnel to go under Lake Shore Drive and access the walking/biking paths.

Dinner on the town: Explore North Pond

North Pond, Lincoln Park

When you're in 'the big city,' there's no better dinner option than adding a Michelin Star to your resume! We had the most phenomenal dinner at North Pond in Lincoln Park - certainly the highlight of our weekend. With a perfectly relaxed atmosphere in a gorgeous Arts & Crafts setting, you won't want to skip the wine pairing.

North Pond interior, Lincoln Park

Chicago Shopping

The Magnificent Mile

Working our way up Michigan Avenue!

It goes without seeing that shopping MUST be in on your "weekend in Chicago to-do list!" For starters, no matter how many times you've visited the windy city, you'll have to explore Michigan Avenue, "The Magnificent Mile." The Mile has shifted south over the years, toward the Chicago River. Toward the southern end, you'll find my favorite Nordstrom in the world. If you work your way north from there, you'll find statement stores from nearly all of your favorite brands, from Burberry to Cartier, Louis Vuitton to Gucci.

Grabbing the classiest lunch break on The Magnificent Mile

Ralph Lauren store, Michigan Avenue, Chicago

If you're in the mood for a splurge, stop by the Ralph Lauren store, not just to explore one of the most tasteful home and clothing stores you'll find anywhere, but also for lunch at RL Chicago! If you're lucky, expect a celebrity sighting or two!

Oak Street/The Gold Coast

For my money, the best shopping in Chicago is actually a bit north and west of the heart of the Magnificent Mile, up toward Chicago's Gold Coast. Here you'll find, north of Bloomingdale's, everything from Hermes to Barbour, Chanel to St. John. And if you aren't in the mood to buy, there's plenty of window shopping to be had at some incredible jewelry stores. Grab lunch or drinks at Gibson's.

See a show!

The Chicago Theater (stock)

Stop by the iconic Chicago Theater, not just to take a picture of beautiful signage, but to see a show you can't get at home!

Chicago Sight Seeing

Art Institute of Chicago

The Art Institute of Chicago

The Art Institute of Chicago is the highlight of any trip to Chicago. Located on the southern end of Michigan Avenue, depending on your home base and desire for a stroll, it might be worth cabbing it there or home. No matter how you get to the Art Institute, I promise you won't be disappointed. It's worth every penny. Be sure to check out my favorite exhibit, in the basement, featuring miniature, doll-house sized reproductions of rooms representing life over the centuries around the world, focusing on Western Europe and the United States. Of course, the Art Institute of Chicago is also home to a world-renowned collection of Impressionist classics, including as many of Monet's water lilies as you can see on this side of the Atlantic.

"The Bean" (Cloud Gate)

"The Bean" / Cloud Gate, Millennium Park (stock)

A more recent addition to the Chicago sight seeing agenda is the now-famous "Bean," (2004) also known as its actual name "Cloud Gate." A visit to Millennium Park is free and extremely quick, so don't allocate too much time for your selfie.

While you're here - Stop by Remington's

Before, or after, your visit to The Art Institute of Chicago, be sure to stop by Remington's, directly across from Millennium Park, for their amazing Bloody Mary, which comes with a tiny Miller High Life. I just can't get enough of these and it's become a mainstay of our trips.

Bloody Mary's at Remington's, Chicago

Architectural Boat Tour

Architectural Boat Tour time!

Sticking with the theme of arts and design (and drinking, for that matter), an architectural boat tour is a wonderful way to spend a relaxing afternoon on the Chicago River. You'll board right below the portion of Michigan Avenue that crosses the river, and spend about an hour and a half seeing the city from a new vantage point (and drinking on a boat). There are bars, bathrooms, and knowledgeable tour guides on board.

Thanks for stopping by!

I hope you enjoy your weekend in Chicago as much as we always do! Feel free to drop your recommendations below in the comment section!