The Best of Chicago: Local Fora Advisors Share Their Tips on How to Make the Most of Your Windy City Vacation

One of the benefits of having a global community of Fora Advisors is the insider intel you get for just about everywhere. Following a recent Chicago meet-up, we tapped into the local expertise of some Windy City advisors. Below, you’ll find their recs for where to eat, drink and visit in this Midwestern metropolis.

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Chicago's best restaurants: cafés, taverns, local gems & more

If you’re anything like us, you can’t start the day without something caffeinated (our go-to is always coffee). Fora Advisor Julie Middlebrook-Levin recommends the tiny and charming Sawada Coffee for your morning pick-me-up. Her favorites: the black como latte and the matcha cortado. Another great option, Julie says, is Vietfive, where the beans are grown and harvested from the founder’s family farm in Vietnam. 

If you’re craving a pastry — sweet or savory — to accompany your morning cuppa, head to Mindy’s Bakery, a favorite of Fora Advisor Katie Larsen. Her advice? Go with your family and split the smoked-ham-and-mustard-with-gruyère croissant, and the hot-fudge croissant. 

“Best of both worlds,” she says.

Chicago is brimming with varied cultural influences, which means its food scene is excellent. Here, Italian food is a must. Katie recommends the family-run Club Lago, which opened in 1952.

“Cozy up to the bar for a martini or two and chat with the owner Guido,” she says. “I promise you the evening of your life.”

Julie loves Pizzaria Portafino for pizza and pasta on the riverfront. (She especially loves sitting on their patio during the summer.) For traditional Italian and the city’s best martinis, Fora Advisor Cecily Hedge recommends Club Lucky, also recommended by Fora Advisor Alexandra Shea. 

If you’re craving stellar Indian food and unique cocktails, Julie recommends the hip ROOH, which also serves up fantastic vegan and vegetarian options, she says. Another of Julie’s favorites is GAIJIN, one of the West Loop’s finest for Japanese Okonomiyaki and Kakigori.

“This is a unique and fun casual dining experience that transports you to Japan,” she says. “We lived in Tokyo and can confirm this is authentic!” 

For French-Vietnamese fare in a stylish setting, Le Colonial is the way to go, according to Cecily. And for fun, elevated Chinese-American, she recommends Duck Duck Goat.

Chicago’s Mexican and Mexican-American food scene is also prime. Alexandra says Lonesome Rose is ideal for “a hip vibe, incredible tacos and the longest Mezcal menu I’ve ever seen.” (For more Chicago vibes, she recommends Shaw’s Crab House.) The vibrant 5 Rabanitos, a block away from the National Museum of Mexican Art, in Chicago’s Pilsen neighborhood, is a favorite of Cecily’s. It’s a neighborhood hot spot for some of the best Mexican food. 

But Cecily says her favorite Chicago restaurant would have to be Bavette’s, a cozy, welcoming (and sexy) brasserie. One of Julie’s overall favorites is Avec, a sleek space with a Mediterranean-inspired menu and an A+ wine selection. (Julie says to get the bacon-wrapped dates and pita & dips.)

For a stylish, seasonal New American menu and craft cocktails, Daisies will not disappoint, according to Katie. Pro tip from Katie: while waiting for your table, grab a glass of wine (or a beer, or a cocktail) at the nearby wine bar, Easy Does It.

The best bars in Chicago, from casual watering holes to award-winning haunts

And speaking of bars… Julie recommends The Violet Hour for James-Beard-award-winning drinks amid candlelight (make sure you snag a reservation), the tiki bar Three Dots and a Dash for something fun and group-friendly, The Aviary for a sexy date night (reservations required here, too) and the eight-seat Milk Room for a one-of-a-kind (albeit pricey — but worth it!) experience. More of a Champagne person? Julie loves Pops for Champagne for some post-shopping bubbles (it’s near Chicago’s Magnificent Mile, a prime shopping area).

For specialty liquors, great gin and cocktails paired with popcorn, head to the woman-owned KOVAL Distillery, Julie says. And don’t miss some of their tours and tastings while there. 

Cecily says you can’t go wrong with Booze Box — “part sushi spot, part speakeasy that will transport you to Japan.” Sounds like a fantastic hybrid to us. Sparrow is great for cocktails in what feels like an old hotel lobby, she says, and Cindy’s Rooftop is a must for drinks and a view (one of the best in the city).

And if you like live jazz with your drinks (we do!), Alexandra recommends Green Mill Lounge — once frequented by Al Capone, she says.

What to do in Chicago: yoga, parks, museums & more

The Art Institute of Chicago

There is, unsurprisingly, tons to do in the Windy City. But our advisors have kindly done the heavy lifting and narrowed down the best options. 

Alexandra recommends walking The 606, an abandoned rail line that’s now a green space perfect for exploring local neighborhoods and Wicker Park. Alexandra’s pro tip: grab a coffee at Ipsento 606 to accompany your walk. 

“Their Ipsento latte haunts my dreams!” she says.

Also near The 606 is the Zen Yoga Garage, perfect for post-stroll flow, per Alexandra.

Both Katie and Julie recommend learning about the city’s architecture by river cruise. Katie loves the Lake & River Architecture Tour organized by Wendella’s Boats, and Julie loves The Chicago Architecture Center’s river cruise — but you really can’t go wrong with either. (The Women in Chicago Architecture and Walk Pilsen tours are some of Julie’s other favorite tours run by the Architecture Center.)

And the museums! Chicago has some serious museum game. The Art Institute of Chicago, the Field Museum and the Museum of Science and Industry, Chicago are among Cecily’s go-to institutions. Alexandra recommends 21c Museum Hotel Chicago, a rotating art gallery free to the public (always a plus). Julie’s favorite is the Museum Of Contemporary Art Chicago, where, on Tuesdays, you can peruse the bustling farmers’ market on the MCA plaza. Contemporary art and local produce? Sign us up.

The city also boasts an impressive amount of green spaces. Maggie Daley Park, Alexandra says, is great if you’re traveling with kids: there’s a playground, a climbing wall, mini golf and, in the winter, ice skating (with hot cocoa, of course). 

Cecily recommends wandering around the ponds at Lincoln Park, and popping into its namesake zoo — which is free (!). For Katie, the 385-acre Chicago Botanical Gardens, a bit north of the city, is the perfect nature escape.

Kayaking on the river is another highly recommended activity from both Julie and Cecily. If you want something guided, Julie’s go-to is Urban Kayaks. She especially enjoys their Historic Chicago Tour. Needless to say, our bags are packed.

Ready to travel? Connect with Fora to plan and book your Chicago getaway today.