hannah's guide: chicago

a local's perfect weekend in the windy city

when to go…

Late May through October is Chicago at its purest and prettiest with warm lake breezes, sun-soaked patios, and that electricity in the air that makes you understand why people fall hard for this city (and don’t leave after winter hits). September might be the sweet spot where it’s not too humid and the summer rush starts to die down a bit.

If you’re escaping a bleak winter elsewhere, don’t overlook March and April. They’re unpredictable, yes, but you can catch some of the first warm days when the whole city collectively thaws and heads outside to celebrate the good weather. It’s a very Chicago kind of joy.

I’d avoid visiting in the deep winter unless you’re coming specifically for holiday magic. The Christmas lights are stunning, but the cold is no joke. Wind off the lake humbles me every year.

One thing before you pack: Chicago weather changes its mind constantly. Dress like you’re preparing for three seasons at once and prepare to walk because you’ll be doing a lot of it.

where to stay…

• Chicago Athletic Association - The Loop

• The Ambassador Hotel - Gold Coast

• The Claridge - Gold Coast

• The Hoxton - West Loop

• The Robey - Wicker Park

• Sable at Navy Pier - Streeterville

friday.

Ease into your weekend with neighborhoods that know how to have a good time – Gold Coast and River North.

Start with dinner at Le Colonial, a transportive experience filled with French-Vietnamese staples and fun cocktails. If you want something richer and more classic, book Bavette’s Steakhouse for the best steaks, shrimp cocktail, and an old fashioned.

After dinner, you can wander toward the “Top of the Triangle” for an after dinner drink at Gibsons Bar & Steakhouse, Hugo’s Frog Bar & Fish House, or LuxBar. All are buzzy, crowded, and great for people watching.

You can always end your night with a martini at RL Bar and order a late night burger (the best in the city!).

saturday.

Start your day in Old Town at Doma Cafe and for their Cevappi and buttermilk pancakes on their back patio.

From there, begin the city’s best walk. Meander east through Old Town on Wells Street into the Gold Coast’s tree-lined streets until the neighborhood opens into Lincoln Park. Keep walking north and you’ll naturally flow right into the park itself. On Saturdays beginning in April, you can walk through the Green City Farmers Market to stop for your second coffee of the day and a local pastry.

Continue your walk east until the park meets the lake. From here, pick up the lakefront trail, a breezy path that hugs Lake Michigan and winds north and south past beaches and sailboats. I would head south and follow it until you reach Grant Park, the city’s front lawn. This is the perfect place to take a breath, and then call a cab to the West Loop and the Fulton Market district.

Once you arrive in the West Loop, you can really pick your pleasure. This neighborhood is full of shopping and restaurants so you could have a late lunch or dinner here. Some of my favorites are:

• Publican Quality Bread - More pastries + coffee

• Tempesta Market - The best sandwiches in the city

• Bisou - Fun for a pre-dinner cocktail

• Monteverde - I am passionate about this place. Get the Burrata e Ham and the Gnochetti con Pesto.

• Elske - Refined, thoughtful Scandinavian-inspired dishes

• Maxwell’s Trading - A buzzy new-age american restaurant

• Au Cheval - The burger everyone has to try once

• The Publican - A standout with locally and seasonally sourced ingredients from around the Midwest. Nothing on the menu here is bad.

sunday.

Sunday morning spent in Wicker Park and Bucktown is a good way to ease into your last day.

Start at the Wicker Park Farmers Market (Sundays) for more local vendors and artists. Then head to Middle Brow Bungalow for sourdough-everything: pizzas, bagels, pastries. Plus they brew their own beers, wines, and coffee.

If you’re feeling ambitious, you can pre-order the famous breakfast sandwich from Kasama, or go big and attempt a lunch reservation for the most unforgettable Filipino tasting menu. For something classic, I would try Le Bouchon, a tiny French bistro that feels straight out of Paris.

In the afternoon, head east for shopping and strolling in Lincoln Park down Armitage street. I love popping into The Kismet Table and Found by Steph.

For lunch I love:

• Athenian Room - Get the Greek salad + chicken Kalamata

• John’s Food and Wine - Great sharing plates

• Denucci’s - A modern Italian spot and the best negroni in the city

• Galit - Delicious mediterranean and another sharing plates option

Another area not too far from here is Southport Corridor which is adorable for walking, shopping, and hopping over to Wrigleyville bars if that’s your speed.

anytime things to do…

If you’re looking for things to do beyond eating and strolling, Chicago always has something happening. I highly recommend booking a ticket to a show at The Salt Shed, the best outdoor venue. In the summer, you’ll stumble onto street festivals, neighborhood block parties, and food events nearly every weekend so check the schedule. You can spend an afternoon wandering through the Lincoln Park Zoo, one of the only free zoos in the country, or take the iconic Chicago Architecture River Cruise to see the skyline from the water (it’s touristy for a reason but one of the best ways to understand the city).

honorable mentions…

• Loba - My favorite pastries and coffee in the city. Try to go on Sunday for their Mole Croissant.

• Lula Cafe - Logan Square brunch royalty

• MingHin Cuisine - The best group dim sum

• Giant - Inventive and delicious dinner

• All Together Now - Strong coffee and fun brunch plates

• Little Goat Diner - Modern southern brunch

• POSH - Like walking into a dream. A great place to shop for a gift or just browse.

• Space519 - A lunchroom and shop tucked away in Streeterville

• Slant of Light Books - The sweetest bookshop in Old Town owned by a woman named Jess and her Golden Retriever, Geordi

• La Fournette - An authentic french bakery located right next to Slant of Light Books in Old Town

• Green Florist - A mainstay family-run shop with the most beautiful arrangements, I pop in here sometimes just to smell the blooms

  *You can find a members-only map of every place ever mentioned in our guides here!