Chicago, the Midwest’s largest and most cosmopolitan city, is more than a big sports town and business hub. It is a sophisticated, world-class metropolis with cultural attractions to suit every taste. For many visitors, all paths lead to the Loop (Chicago-speak for downtown) and Navy Pier, a lakeside destination popular with out-of-towners, featuring restaurants, shops and exhibits.

Beyond those tourist-packed haunts is a new mecca. Bucktown: a quiet up-and-coming neighborhood north of Wicker Park on the city’s northwest side. Antique and art galleries and an eclectic mix of stylish shops and restaurants have taken root here in historic buildings along North Damen Avenue. This charming enclave is emerging as one of the city’s most intriguing districts, buzzing with newfound energy.

Begin by exploring the area at Toast Two, arguably Chicago’s best spot for breakfast and well worth the wait for a table. Try French toast stuffed with chocolate, strawberries or Mascarpone cheese then dusted with powdered sugar; filet mignon with eggs; or a Cobb Club, a grilled tenderloin sandwich with roasted shallots and freshly-made soup.

Afterwards, make your way down to Virtu, which sells beautiful, handmade treasures like jewelry by designers from New York, San Francisco, Maine and Rhode Island; blown-glass vases and bowls; handmade cutting boards rendered in Wisconsin bird’s-eye maple; and exotic tea sets and coffee-table books on tea. For exquisite leather goods and quality furnishings, visit Stitch. The shop boasts an impressive array of desk accessories, handbags, satchels, belts, photo albums and even pillows. The museum-quality collection of Chinese, Tibetan and Southeast Asian antiques at Pagoda Red will please even the most discriminating connoisseur. Then, for a quick lunch, grab an inexpensive but delicious burger at Bar Louie.

Bucktown’s good taste encompasses fashion too: Malabar, a men’s and women’s boutique, is the place for smart assortments of high-end yet affordable clothing from European-influenced local designers. Trendy Apartment Number 9 is a must-see boutique for GQ-types, while Tangerine has fashionable offerings that will make style mavens swoon. For the little ones, PsychoBaby offers “cool, crazy kids’ stuff” per the store’s motto, including hip clothing for boys and girls. You’ll also find wooden and metal toys that conjure memories of your childhood and even classic Birkenstocks, Vans and Converse “All Stars” for tiny toes.

After you’ve grown weary of shopping, stop in for dinner at Spring, a popular eatery set in a 1910s Russian bathhouse that dishes out Asian-influenced American fare with an emphasis on seafood. Restaurant partner Shawn McClain was named “Chef of the Year” in 2001 by Esquire magazine. Later, unwind at Meritage Café and Wine Bar, a romantic spot with dim lighting, soft music and an all-American wine list-it pours more than 20 vintages of vino by the glass-or try Café Absinthe, a longtime Bucktown fixture where you can enjoy a nightcap. They have a great selection of scotches and cognacs you can sip at a plush leather banquette or candlelit table.

Finally retreat to your room at the luxurious Four Seasons Hotel, park yourself in the perfect-for-lingering chaise lounge, and enjoy the late night views of Michigan Avenue or Lake Michigan or both if you book a 25-series executive suite. After getting your urban fix, return home and begin planning your next day-long getaway.

What & Where:
Toast Two (2046 N. Damen Ave.; 773-772-5600)
Virtu (2034 N. Damen Ave.; 773-235-3790)
Stitch (1723 N. Damen Ave.; 773-782-1570)
Pagoda Red (1714 N. Damen Ave.; 773-235-1188)
Bar Louie (1724 N. Damon Ave.; 773-645-7500)
Malabar (1880 N. Damen Ave.; 773-321-6685)
Apartment Number 9 (1804 N. Damen Ave.; 773-395-2999)
Tangerine (1719 N. Damen Ave.; 773-772-0505)
PsychoBaby (1630 N. Damen Ave.; 773-772-2815)
Spring (2039 W. North Ave.; 773-395-7100)
Meritage Café and Wine Bar (2118 N. Damen Ave.; 773-235-6434)
Café Absinthe (1954 W. North Ave.; 773-278-4488)
Four Seasons Hotel (120 E. Delaware Place; 800-332-3442)

For more information about Bucktown, visit


Follow 52 Perfect Days on
Bloglovin | Facebook | Twitter | Pinterest | Instagram

This post may contain affiliate links, which means that if you click on some of the links in this post and purchase something, I might receive a commission. This is a good thing! There is no additional cost to you and I make a tiny bit of money to help fund this website! 

If you liked it, please share it. Thank you!