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Independently owned and operated, Bob Chinn’s has been serving up incredible seafood and steaks for over 25 years. Featuring the freshest of seafood, flown in from places as far off as Alaska, Hawaii, and New Zealand, you will find yourself in a fresh fish heaven upon arrival. This one-of-a-kind dining experience is unique to the sole location on Milwaukee Avenue. Come for work or play, with friends or family, there’s a little something for everyone on the menu at Bob Chinn’s.

From the outside, it even looks like a miniature dollhouse. With pastel yellow paint, a cute porch, and a tiny entrance, Shirley’s Dollhouse almost makes you feel like a kid again. Venture into one of the five rooms that are literally stuffed with all your doll needs, and sift and sort your way to that exact piece that you so desire. You might even come across that missing item that you haven’t been able to find since you were just a wee tot. And should you have a special tiny companion from your youth in need of a little TLC, you can have them repaired and back to full health before you know it. Shirley’s is surely the spot for all things ‘doll.’ Shirley’s Dollhouse, 971 N. Milwaukee Avenue Building 2, Wheeling. 847-537-1632

On a quiet residential street one block from the popular vintage shops, bars, and restaurants of Milwaukee Avenue, the Wicker Park Inn is one of the best values in Chicago, attracting an eclectic clientele of older couples, families who book the whole place for weddings and other special occasions, and young travelers eager to live like a local amid the vibrant culture of the Wicker Park and Bucktown neighborhoods.

The entire Forest Preserve District encompasses 68,000 acres, and includes about 11 percent of Cook County, so there is literally a lot of ground to cover. Your best guide to navigating the preserve will be the maps located on their website listed below. This particular entrance can be found off of Dundee Road just a bit east of Milwaukee Avenue, near the town of Wheeling. There are plenty of open fields to walk through, ponds to sit by and read a book, and trails to wander should you feel like getting a little exercise. The Des Plaines River snakes it way through this particular part of the preserve, which is an added bonus when making your way through the scenic forest.

It’s always been about affordable vintage goods at this Wicker Park boutique, which sells contemporary dresses and tops from Amuse, men’s hats from Brixton, denim from skinny-jean pros Just USA, rompers from Los Angeles–based En Crème, and handcrafted leather boots from Red Wing. The popular shop’s homewares and apothecary section is arguably the best place to pick up gifts your friends will love, from grooming and shaving goods to candles, perfumes, and barware like flasks and cocktail shakers.

Established in 1963, Sale Barn Square Antiques is touted as the largest and oldest antique boutique in the greater Chicago area. Their services range from appraising and buying select items, to jewelry valuation, and they can even help with your estate needs should they come up. So mosey on in to the boutique barn for a gander at all things whimsical and fun. You might be surprised at what you find.

A good used bookstore is a glorious thing and Myopic is one of the great ones. They have a giant selection of new, used, rare and out of print books on 3 floors, they’re well organized, they’re open until 11pm and there’s a store cat! There’s also a small reading room on the top floor with a big wooden table and chairs and they host poetry readings and live music. They’re open until 11pm all week long but there’s no public bathroom so factor that in to your afternoon of browsing.

Wanna be a redhead today? Maybe green is more your color… or something in a sensible silver? Long hair, short hair, punk rock styling, Farrah Fawcett flips, a cute bouffant or perhaps a conservative bob, Heads and Threads has got it and you know you want it. Buy a 50 cent wig cap and try on three wigs just for fun. Buy something or don’t, but I think those false eyelashes just caught your eye and maybe you need a glittery tiara to go with it? I’m just saying… Start here for your Halloween shopping and base the whole costume around your wig. Why not, right?

Located in Logan Square, and featuring one of the more eclectic wine lists I’ve seen in a while, Telegraph Wine Bar is the perfect place to swing by for a leisurely bite to eat and drink. The antique fixtures and lights provide a bit of a speakeasy vibe, and the rustic double bar and hardwood furniture definitely make you feel right at home and safe from prohibition-era raids. As you sip your craft drinks, unique wine, or small batch beer, enjoy indie tunes in the background. If you want a real local bar with a speakeasy feel, there’s a seat at the bar with your name on it. If you’re planning on having dinner as well, the menu is meat-heavy, which is not necessarily a bad thing unless you’re vegetarian. The desserts are sizable enough to feed your party of four, if you even want to share (it’s that good).

A group of Chicago artists took over the Flatiron building in Wicker Park and turned the triangular building into an art gallery comprised of 2 floors worth of unique art studios. In this building artists can rent gallery space to work and display their art and they have artistic control over the room, the halls, the ceilings and even the floors. The entire building is now an artistic wonderland and even if you don’t buy any of the art pieces, it’s worth a walk through just to see the creativity on display here. The Flatiron building is open all day and there are always artists in their galleries working, selling and willing to talk to visitors. The first Friday of each month is the best time to visit because all the artists open their studios between 6-10pm and turn the neighborhood into a block party. Go support a local artist and have a glass of wine. It’s good for everybody.

What started as a hobby by Fred Koehler and his wife back in 1975, has turned into something that we all now reap the benefits of. Lynfred Winery was founded in 1979 in Illinois, of all places. Urged by some to take his talents to California, Fred refused to leave his roots and set up shop in Middle America. Over the years Lynfred has produced some award-winning vino, some of which you can sample in their tasting room in Wheeling. Grab a glass or a bottle and make yourself comfortable on the grassy lawn outside, or settle into a comfy chair in the tasting room/wine shop inside. Varietals range from Pinot Grigio to Viognier all the way to Syrah and Cabernet Sauvignon. Grapes are sourced from all over, with an abundance from California, and even a few from Washington and Chile as well. A visit to Lynfred Winery is the perfect way to while away a couple of hours over a nice glass (or two) of wine.

This charming little store on Milwaukee is stuffed with vintage goods in primo condition. Beautiful chunks of costume jewelry and frilly fascinators share space with lush leather handbags and sparkling glassware. Nothing in the store is cheaply made—or priced—but all of the items are carefully selected for maximum appeal and quality. Shoppers who come in to browse will likely find treasures they simply can’t live without, because Store B Vintage has some of the prettiest retro pieces in the city.