A Chicago Local’s Guide to the Perfect Long Weekend

3 days ago 14

Welcome to Like a Local, our recurring series where travelers share their perfect long weekend itineraries—from the coffee shops and cocktail bars they swear by to the hidden corners worth wandering. This week, Chicago resident, Caroline Bratney focuses on the city's architectural highlights.

Welcome to beautiful Chicago! I’ve lived in this Midwestern metropolis for ten years and have fallen in love with so much of what this broad-shouldered city has to offer.

There are many ways to experience the Second City to None; this travel guide has downtown roots but includes neighborhood visits and an overall emphasis on the city’s unique architectural, urban, and natural beauty. I’ve generally avoided touristy spots or widely heralded restaurants to give you an experience that a local would truly appreciate. I’ve assumed a Saturday-to-Monday timeline, each stop is accessible by foot, bike, or public transit, and I’ve got my fingers crossed for good weather.

Where to Stay:

Home base is the Chicago Athletic Association, formerly a fitness club for Chicago’s wealthiest citizens, but now a veritable campus of places to eat, drink, and sleep. You’ll love the lakefront view from the rooftop bar at Cindy’s, but if you’re more of an indoor cat, you might prefer the Beauty and the Beast-esque Drawing Room, the rambunctious shuffleboard kingdom at the Game Room…or maybe the Shake Shack. I’ve staycationed there myself, so the CAA is tried and true for this local.

Breakfast at Venteaux Brasserie

I love Venteaux for its beauty and versatility—it’s a consistent hit for our Chicago visitors. Whether you’re craving king crab for brunch or just to pop in for some coffee and a pastry, Venteaux has it all and everything in between. Plus, its café and restaurant are stunningly beautiful, with colorful Art Deco motifs throughout.

Architecture Tour

Behold: the only real tourist activity I’m including—even the locals love this experience. This particular tour is hosted by extremely knowledgeable Chicago Architecture Center docents, and you can feel the love they have for the city while enjoying a peaceful boat ride on the Chicago River—all with refreshments in hand.

Lunch at 3 Arts Club Café

Enjoy a leisurely walk through the stunning Gold Coast neighborhood (the area around Rush and State Street has particularly great vibes). It’s full of magazine-worthy homes and what appears to be just a Restoration Hardware store. But inside, you’ll find the 3 Arts Club Café, where chandeliered ceilings and gobs of natural light invite you to enjoy any number of craveable entrées, from brunch fare to shockingly good sandwiches to a whole grilled branzino. You’ll want to bring your mom with you next time.

Coffee at Ralph’s Coffee

I’m not sure I’d ever been inside an actual Ralph Lauren store until Ralph’s Coffee pulled me in with its devastatingly photogenic appeal. It’s perfect for a posh pick-me-up.

Newberry Library in Washington Square Park

Take your caffeinated beverage (or ice cream cone) from Ralph’s for a 10-minute walk northwest and you’ll find the grand Newberry Library, situated at the north end of Washington Square Park. Enjoy free admission, a guided tour, a visit to the bookshop, and (fingers-crossed) some sunshine in the park.

Cocktail at Brass Tack

I’m so smitten with the deco finishes inside Brass Tack—the restaurant inside the Waldorf Astoria—that my husband and I did a photoshoot there for our ten-year wedding anniversary. Drink one for me!

Dinner at Siena Tavern

I’m not saying you shouldn’t have dinner at Brass Tack, but if you catch the southbound 36 bus, you’ll be right at Siena Tavern, where you can get one of my favorite dishes in the city: the spaghetti with lemon cream and lump crab. You’ve been very active today, so you might need to double-carb with a side order of parmesan frites, too. I hope you’ll walk home by way of the beautiful Wrigley Building and enjoy your walk across the river under the twinkling city lights.

Breakfast – A Bagel

I know what you’re thinking—and no, I do not pretend to contend with the greater bagel capitals of the world. Still, there is something to appreciate about Chicago’s bagel scene, and I narrowed it down to three Brown Line accessible-locales, depending on how long you can wait to eat breakfast after leaving the hotel.

Schneider’s Deli: Located in the adorable Ohio House Motel, this deli offers the peak experience otherwise known as egg everything bagels.

Chicago Bagel Authority: A totally different vibe. Casual, college-y, and focused largely on the steamed bagel sandwich, of which they have numerous, down-home iterations. This includes the beloved egg everything bagel on which my recommendations largely hinge.

Bagel Miller, but this place is ridiculously cute AND located IN the ridiculously cute neighborhood where we’re about to spend some time. I also love their creative, slightly fancier, bagel sandwiches, like the “Joni” (bacon, cucumbers, nori, chili crisp, and scallion cream cheese—and it’s worth the splurge to add some smoked salmon to the mix).

Explore Lincoln Square

I’ve heard it said that Lincoln Square is the Stars Hollow of Chicago—a walkable, storybook community full of desirable amenities. A few favorite stops of mine are The Book Cellar, Gene’s, and Neighborly, and I think you’ll love Oromo Café.

Lunch at Maison Marcel

Hop back on the Brown Line for lunch at Maison Marcel, the sweetest little French café with a true Parisian aesthetic. I love the smoked salmon tartine, but there are plenty of options if you already hit your salmon quota with your bagel breakfast.

Choose Your Own Adventure in Lakeview

Lakeview East: Walk north on Broadway for Unabridged Bookstore and the impressive pantry at The Coffee and Tea Exchange.

Southport Corridor: Head west on the Belmont bus to Southport and explore northward for boutique shopping (Alice and Wonder is my fave). Then catch a flick—or simply feast your eyes—at the historic Music Box Theatre. Music lovers may prefer to take the Belmont bus to Lincoln/Ashland for Chicago Music Exchange. Either way, you shouldn’t NOT stop at Ann Sather for a cinnamon roll to enjoy when hunger strikes.

Lakefront Views: Bicyclists will appreciate the Divvy station at Barry and Broadway near Maison Marcel—it’s only a 7-minute ride to Lincoln Park’s famed North Pond, and the Lakefront Trail can’t be beaten on a beautiful day.

Dinner at Pequod’s via Ashland Bus (or your Divvy) You knew there’d be pizza. While locals famously disdain deep dish, I’ve found that Pequod’s—with its glittering caramelized crust—is the exception. This is not a meal that can be rushed, so settle in and take your time—I promise it’s worth the wait.

Drinks at Armitage Alehouse Head east on Webster and south on Sheffield to a dreamy little strip of Lincoln Park on Armitage, where you can enjoy the libations at the famed Armitage Alehouse. When you’re ready to head home, the North/Clybourn Red Line stop will get you there.

Breakfast at Valois

Hit the ATM and take the 6 bus southbound toward 79th/South Shore to Hyde Park and 53rd, where you’re just a few minutes from Valois, one of the oldest cafeteria-style restaurants in the country. I’ve only been there for lunch, but anywhere Anthony Bourdain and Barack Obama can both vouch for is a place I’d eat any time of day. Grab your tray and get in line for a nostalgic, cash-only breakfast!

Explore Hyde Park

Hyde Park is home to exquisite architectural beauty, including the University of Chicago (petitioning to rename Harper Memorial Library to Southside Hogwarts) and Frank Lloyd Wright’s Robie House. You can make it to that area on foot through the neighborhood, or take a load off and board the 55 or the 171 bus.

Lunch in Jackson Park

Amble along the Midway Plaisance but briefly cut north to pick up some Seoul Taco (turns out, bulgogi wants to be in a tortilla) to enjoy in sprawling Jackson Park. If you’re up for it afterward, head north of the park to behold the scenic Promontory Point. Weather sites include southern classics at Roux (very busy during college brunch hours!) or a little bit out-of-the-way trip to timeless Harold’s Chicken.

Coffee at La Boulangerie and Co.

Before taking the 6 bus back into the city, stop at La Boulangerie and Co. for coffee and a pastry—their butter croissants are my favorite in town!

Dinner at Cindy’s Rooftop Bar

Once you’ve made it back to headquarters at the CAA, the goal is a low-key, relaxing night to round out your long weekend. In this spirit, prepare yourself for one of two experiences: 1) a fancy little dinner at Cindy’s Rooftop Bar atop the hotel, or 2) ordering from the Shake Shack downstairs and eating it in bed. Or both. It’s your last night of vacation, so—do you, babe.