This is an on-going guide based on my favorite places in Chicago. Click on a picture to read one of my prior posts about the area. Bike and el train directions are general. Refer to the Chicago Bike Map for the best routes.
On the east side, accessible from anywhere in the city. A great bike ride, although it may be very crowded in the summer and icy in the winter.
Bike: Take the Lakefront Trail and then lock up and walk around, or take Wells Street bike lane from the north. El: Any line takes you to the loop; which stop you take depends on your destination.
The Magnificent Mile: Saks Fifth Avenue, Nordstrom, Macy’s, lots of designer and mid-range boutique.
State Street – Theatre District: Fabulous discount shopping around State and Randolph Streets. Nordstrom Rack, Loehmans, H&M, Old Navy. A huge Macy’s that used to be the original Marshall Fields.
Goodman Theatre, 170 N Dearborn St. – Come here for world-class plays. Tickets for $25 on the upper side boxes – just lean over in your chair on the railing for a view of the stage.
Chicago Theatre, 175 N. State St. – A great photo op of the iconic “Chicago” sign. Lots of big-name performers have concerts here, so check the calendar before coming.
East Lakeview, Wrigleyville and Boystown
Bike: Lakefront trail or bike lanes on Clark, Halsted, Southport and Lincoln. Lots of quiet side streets to cycle on, but some end abruptly. El: Many stops on the Red and Brown lines.
Unabridged Books, 3251 N Broadway – I could spend hours in this big independent bookstore with lots of quality handwritten info tags (you can tell they love books). Large selection of gay and lesbian titles.
Haystack Vintage, 2934 N Broadway – One of my favorites. A well-edited vintage store with a great selection of clothes, shoes, housewares, jewelery and some bikes and furniture. Reasonable prices.
Clothes Optional Vintage, 2918 N Clark St – Another good vintage store, although I don’t always find something. Mostly clothes and shoes, both men’s and women’s.
Bike: Southport has bike lanes north-south; Roscoe is a nice route east-west. El: Brown line to Southport stop.
Anthropologie, 3532 N. Southport – A national chain store with higher prices, but their housewares and clothing are super pretty. Like a magical but really expensive thrift store. I’ve never actually bought anything from here.
Ann Sather, 3416 N. Southport – Swedish restaurant with breakfast all day and delicious freshly baked cinnamon rolls. A Chicago tradition.
Justin’s, 3358 N. Southport – A cozy neighborhood pub on the corner of Southport and Roscoe. Large beer garden in the back.
Julius Meinl, 3601 N. Southport – Austrian cafe with delicious brunch and pastries. Coffee comes in a small cup with a tiny glass of warm water and a cookie.
Southport Grocery, 3552 N. Southport – Small market for high end specialty foods. Cafe in the front with yummy brunch and famous cupcakes.
Sensational Bites, 3751 N. Southport – The best cupcakes in Chicago! I heartily recommend the Boston Cream cupcake.
Candyality, 3428 N. Southport – Super fun old-fashioned candy store. Buy a mix and they will tell you your “candyality” personality profile, like psychoanalysis but with gummy bears.
Music Box Theatre, 3733 N. Southport – Movie theatre playing an interesting mix of independent and foreign films. Sometimes they have midnight showings. Check their website for listings.
Bike: Marked shared lanes on Lincoln will take you directly there, or take the nearly deserted Ravenswood Avenue along the railroad and then go west on a neighborhood street, Sunnyside. El: Brown line to Western stop.
Laurie’s Planet of Sound, 4639 N. Lincoln Ave – My favorite record store. Excellent selection of CD’s, new and used vinyl, DVD’s and magazine. Friendly staff.
Book Cellar, 4736 N Lincoln Ave – A small neighborhood book store with a wine bar inside. I am the target market. You may not find what you’re looking for, but you will find something you like.
Sacred Art, 4619 N. Lincoln – Locally and independently owned art store. Come here for fun work that you can actually afford. Lots of Chicago-themed pieces.
The Chopping Block, 4747 N. Lincoln Avenue – Admire their fancy cookware, then buy a $20 garlic press and escape before you buy something you can’t afford.
Merz Apothecary, 4716 N. Lincoln Avenue – A shop for all sorts of lotions, shampoos, soaps and candles. Lots of European products, all price ranges.
Timeless Toys, 4749 N. Lincoln Avenue – Awesome old school toy store. My nephew loves this place.
Chicago Brauhaus, 4732 N. Lincoln Avenue – Old school German restaurant (carpet! wood paneling!) with delicious schnitzel and mashed potatoes. Steins of beer. Accordion-led band with singers every day. Small dance floor with old couples and children busting a move.
The Grind Cafe, 4613 N Lincoln Ave – Small and cozy coffee shop with delicious baked goods and fantastic coffee. The tables are often full on weekends, so you may need to take your drink to go and stroll down the Square or wait for someone to leave. Free Wi-Fi.
Bike: Go straight up the bike lanes on Clark Street the whole way, or start on Southport Avenue’s bike lanes and then get on Clark when Southport ends. El: Red line to Berwyn or Bryn Mawr stops.
Icosium Kafe, 5200 N Clark St – Casual Algerian creperie. Delicious savory and sweet options. Get a pot of tea to go with it.
Kopi Traveler’s Cafe, 5317 N. Clark St. – Coffee shop with sandwiches and pasteries. They take your order at your table and bring it to you. Small section in the back with international tchotchkes and travel guides. Live music on Mondays.
In Fine Spirits, 5418 N Clark St. – In the tradition of classic cocktail bars. Very friendly and spiffy place. Try their absinthe fountain (tastes like strong black licorice) and dinner menu, then visit their wine and liquor shop next door. Check their website for frequent tasting events.
Women and Children First, 5233 N Clark St. – Bookstore specializing in female authors. Another favorite of mine. Good ‘zine and children’s section.
Bike: Damen bike lane, Roscoe Avenue very bike friendly, lots of side streets. El: Brown line to Paulina, walk west down Roscoe Avenue.
Roscoe Village Bikes, 2016 W. Roscoe – Neighborhood bike shop owned by a married couple and their sweet dog.
Kitsch’n, 2005 W. Roscoe – This restaurant is not perfect but if I’m on Roscoe looking for brunch, I most often end up here, eating fried chicken and waffles that I could find much better at Chicago’s Home of Chicken and Waffles (3947 S. King Drive). They serve tasty Intelligentsia coffee.
Volo Wine Bar, 2008 W. Roscoe – I would skip this place for dinner, but it’s a lovely spot for a glass of wine and a cheese plate. Beautiful back patio if the weather is cooperating.
Scooters Frozen Custard, 1658 W. Belmont – Delicious frozen custard, a neighborhood gem. Closes for the winter the first Friday after Thanksgiving weekend.
Pho’s Hot and Spicy Thai, 3332 N. Lincoln – The restaurant I frequent the most, usually for take out. A wonderful hole in the wall, don’t let the shabby exterior dissuade you. The medium spicy is very spicy! BYOB with no corking fee.
Dinkel’s Bakery, 3329 N. Lincoln – An old German bakery, this is my favorite place for sweets. The best donuts in town!
Four Moon Tavern, 1847 W. Roscoe – There are a lot of neighborhood pubs in this area: Four Moon is my favorite. Good, greasy food and a selection of well-priced beer. Very laid back, divey in a good way.
Turquoise, 2147 W. Roscoe – Nice Turkish restaurant, white table cloths and candles but don’t be shy wearing jeans. Best if you can eat here for lunch during the week, as the prices are much lower.
Hard Boiled Records, 2010 W. Roscoe – Buy the music here that you can’t find anywhere else. Don’t try to buy the music that you can find at other stores, because they won’t have it.
Shangri La Vintage, 1952 W. Roscoe – Small and well-edited vintage shop with friendly owners. This is the kind of place where I leave with one perfect and inexpensive piece each time, not with an armful.
Dutch Bike Chicago, 651 W Armitage Ave. – The name says it all. Oma’s original home, great people, beautiful bikes.
Lululemon Athletica, 2104 N. Halsted St. – My favorite place for stylish and comfortable yoga clothes. Expensive, so I recommend sticking to the sales racks in the back room. They occasionally have free yoga classes.
Nookies Too, 2114 N Halsted St. – Great casual brunch, well-priced for the area. Be prepared to wait on weekends.
Bucktown and Wicker Park
Earwax Cafe, 1561 N Milwaukee Ave – Casual, fun atmosphere, delicious turkey burgers and fries. Small, so there may be a wait. BYOB. Cash only, but there’s an ATM inside.
Milk and Honey, 1920 W Division St – One of my top three brunch spots in the city. Everything is delicious, especially the granola, which I buy bags of and eat at home. Don’t freak if there’s a long line: you line up at the counter to order and they usually can seat you as soon as you order.
Eskell, 1509 N. Milwaukee Ave. – Boutique clothing shop selling trendy and somewhat unique pieces. The reason to stop by is the rack of perfectly edited vintage clothes and shoes in front. You’ll pay more than you would at a warehouse thrift store, but the prices are reasonable ($25-$35). After looking around, settle on the couch to flip through back issues of Lula Magazine.
Reckless Records, 1532 W. Milwaukee – The best selection of albums outside of chains like FYE (where you should not buy music!). Lots of new and used vinyl. Very hip and all of that. Friendly staff.
Bike: Lakefront trail will take you right there. Metra: Instead of the el, I would take the Metra train from Millennium Station under the Prudential Towers. It will take you straight there in 10 minutes, but during non-peak times runs only once an hour.
57th Street Books, 1301 E 57th St – My favorite bookstore in Chicago. I no longer live in Hyde Park and this place is quite a trek from the north side, so I combine visits there with trips to see friends in the area. A great bike ride down the Lakefront Trail if you want to explore.
Powell’s Books, 1501 East 57th Street – There is a Powell’s in my neighborhood, but this one is much better. Great used books and magazine selection.
Original Pancake House, 1517 East Hyde Park Blvd. – A chain, but this location does not feel like one. Seriously delicious pancakes and excellent service. There will be a wait on the weekends, but the line goes by quickly and it’s worth it.
For another insider’s guide – with a heavy focus on drinking and biking – check out Being Totally Sweet in Chicago.