10 guides · updated weekly
Shopping guides.
Deep dives into Chicago's neighborhoods, occasions and obsessions: where to go, what to buy, and where to eat after. Written by locals, checked against the shops themselves.
Vintage Shopping in Chicago: Where to Buy and Sell
Wicker Park's Milwaukee Ave resale row, Pilsen's Knee Deep, Andersonville's Brown Elephant, Logan Square's Vintage Frills and the Randolph Street Market.
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Every MICHELIN Restaurant in Chicago
All 100 restaurants in the 2025 MICHELIN Guide Chicago, revealed in November 2025, from Smyth's three stars to 32 Bib Gourmands and 49 Recommended, with notes on which ones sit near our shopping districts.
19 stars · 32 Bib Gourmand · 48 recommended
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The Andersonville Indie Shopping Walk
One slow afternoon up N Clark Street from Foster to Bryn Mawr: the Swedish American Museum, glögg at a 1934 tavern, Chicago-made jeans and T-shirts, a feminist bookstore, a market of 200-plus local makers, records, toys and cardamom buns.
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Chicago Holiday Markets and Lights, 2026
The confirmed 2026 dates for Christkindlmarket and the Magnificent Mile Lights Festival, plus Andersonville's Julmarknad and Lincoln Square's holiday nights, with what to buy and the shops nearby.
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Chinatown Bakeries, Tea and Gifts
A food-first walk down Wentworth Avenue and through Chinatown Square: the neighborhood's oldest bakery, a moon cake and egg tart crawl, bubble tea, herbal teas and dried goods, blind boxes, dim sum, and how to get your parking validated.
Read guide →Gold Coast Luxury: Oak Street and Rush
Which house is where on Oak Street and Rush, which jewelers want an appointment, where to buy and service a Rolex or a Patek, how to plan around the hours and the Nov 21 parade, and where to eat upstairs.
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Chicago Hotels Near the Best Shopping
Eighteen MICHELIN-selected hotels, nine of them with Keys, sorted by the shopping you can walk to: the Magnificent Mile and Oak Street, River North, State Street and Fulton Market.
Read guide →The Magnificent Mile and Oak Street Walk
One long afternoon up North Michigan Avenue from the river past the Water Tower and the vertical malls, then west along the one block of Oak Street where the luxury houses sit, with lunch stops and the Nov 21 Lights Festival.
Read guide →bundle up
Pilsen's 18th Street, Block by Block
An unhurried walk east along 18th Street, from the free National Museum of Mexican Art and its Día de Muertos show past tray-and-tongs panaderías, vintage, vinyl, Chicago's top-ranked bookstore and carnitas counters.
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State Street Holiday Windows and the Walnut Room, 2026
What Macy's has confirmed so far for the 2026 season on State Street, from Holiday Square and Santaland to the Great Tree in the Walnut Room, plus the rest of the street, lunch nearby and the best trains now that State/Lake is closed.
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Wicker Park Records and Books Walk
A day up Milwaukee Avenue from Dusty Groove to the six corners: where to buy and sell records, zines and used books, the resale row by the Damen Blue Line, and the car-free Sunday on Oct 25.
Read guide →Stay in the loop
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