For an indulgent getaway in the heart of Chicago, look no further than Lakeview. A lush hideaway nestled steps from Lake Michigan on the North Side, the neighborhood charms with trendy boutiques, chic restaurants and inviting hotels. Craft cocktails flow at speakeasies nestled amid tree-lined walkups. Michelin-recognized chefs impress at worldly eateries. And in the midst of it all, sports fans make the pilgrimage to historic Wrigley Field to cheer on the Cubs. Here, we present the best that Lakeview has to offer.
Where to Eat
The beloved Radical Reuben at Chicago Diner
3411 N. Halsted St. / Website
“Meat-free since ’83,” proudly proclaims this down-home diner, which has drawn celebs and devoted locals alike with tempting meatless fare like the Radical Reuben with corned beef seitan.
3335 N. Southport Ave. / Website
From housemade pastas to Neapolitan- and Sicilian-style pizza and a smartly curated wine list, this Southern Italian fave is a collab between industry notables Billy Lawless (Gage Hospitality Group) and Ryan O’Donnell (Ballyhoo Hospitality).
See also: The Ultimate Guide To Chicago's Magnificent Mile
Charcuterie at Dear Margaret
2965 N. Lincoln Ave. / Website
Elevated French-Canadian fare showcasing Midwestern ingredients—think fried sweetbreads with stuffed morels and whole-roasted rainbow trout with spring onion vinaigrette—stars at this hit dining destination from executive chef Ryan Brousseau and owner Lacey Irby.
Little Goat Diner’s Shrimp Sammie
3325 N. Southport Ave. / Website
The West Loop’s loss is Lakeview’s gain, as Top Chef winner Stephanie Izard’s beloved downtown spot has relocated to Southport Avenue, offering tempting takes on diner fare like chili crunch burgers, PB&J pancakes and a pork belly sandwich with pickled veggie slaw.
View this post on Instagram
432 W. Diversey Parkway / Website
This subterranean, seafood-focused neighborhood jewel scores with dishes like scallop aguachile with pickled green papaya and Thai basil plus a tiki-forward cocktail menu.
3763 N. Southport Ave. / Website
Possibly the neighborhood’s most beloved BYOB spot, this Argentinean steakhouse and date-night favorite is renowned for its empanadas, steaks and more, all served in intimate, buzzing environs an easy walk from Wrigley Field.
Where To Shop
View this post on Instagram
929 W. Belmont Ave. / Website
Music lovers make pilgrimages to this hip, expertly curated shop for hard-to-find vinyl, CDs, DVDs, games and more.
View this post on Instagram
Southport Avenue between Belmont Avenue and Grace Street / Website
From Lululemon and Paper Source to Alice & Wonder and Krista K, upscale local boutiques and national brands abound on this strollable strip.
View this post on Instagram
3251 N. Broadway / Website
A neighborhood institution since 1980, this inviting shop specializes in LGBTQ+ literature as well as popular fiction and nonfiction, zines, travel and more, with plenty of author readings and book club events to boot.
Where To Stay
3630 N. Clark St. / Website
Across the street from Wrigley Field and boasting a slate of beloved local food and drink establishments like Smoke Daddy barbecue and Big Star tacos, this sleek boutique property just might be the most stylish hotel north of the Gold Coast.
Hit The Town
View this post on Instagram
3733 N. Southport Ave. / Website
A must for cinema buffs, this grand, 700-seat movie house has been packing them in since 1929, and is one of the city’s last movie theaters dedicated to independent, foreign, cult and classic films.
View this post on Instagram
3159 N. Southport Ave. / Website
Considered one of the top small music venues in the nation, this cozy corner spot also serves as a favorite neighborhood watering hole and low-key nosh spot.
View this post on Instagram
1060 W. Addison St. / Website
One of the most stadiums in all of sports and home to the 2016 World Champion Cubs, this 1914 ballpark has been gussied up in recent years but still retains its throwback charm and beloved ivy-colored walls.
Where To Relax
3120 N. Sheffield Ave. / Website
From anti-pollution facials and microneedling to mani-pedis, cupping, massage and injectables, this spa in the heart of Lakeview is a go-to for a wide array of indulgent treatments and beauty services.
Hidden Gem
View this post on Instagram
Between Grace and Byron streets
Inspired by London’s rowhouses on a trip to Europe, realtor Samuel Gross developed this charming one-block stretch of homes between Grace and Byron streets, with each of the 20 homes on one side of the street duplicated at the diagonally opposite end of the block. Completed in 1904, the area was designated a Chicago landmark in 1971.
Check out our Ultimate Chicago Neighborhood Guide here.
Photography by: Dear Margaret photo by Neil Burger; Blue Man Group photo by Kyle Flubacker
