The Run Down

Everyone knows Chicago is one of the best cities for food, comedy and drinks. Tonight, you’ll combine all three for a lively night in the West Town and Wicker Park neighborhoods. You'll start with dinner at a natural wine shop and restaurant for a meal that's described as a fancy picnic. You'll then take in a comedy show at a theater reminiscent of the 1920s Golden Age, featuring ornate Art Deco details, plush velvet seats, and gilded accents. Finish off the night with a drink and a game of pool down the street

1. Dinner @ All Together Now

2. Comedy @ The Den Theatre

3. Drinks @ Little Victories

1. Dinner @ All Together Now

Walking into All Together Now feels like a window into the mind of your bougiest friend. You know, the one who can sniff out the best wine selection from a place you’ve never heard of in France, Spain, or Italy. The one who pronounces all the European stinky cheeses the right way but without any annoying pretentiousness. The one whose playlist is unironically filled with upbeat old-timey jingles that fit their vibe perfectly.

The space is small, with only a few tables and seats at the bar. We definitely suggest making a reservation, as the space is intimate and will make you feel how just the right amount of wine does — comfortable, ready to have a good conversation, and a little more carefree than you were an hour ago.

If your table isn’t quite ready yet, don’t be surprised if you’re offered a complimentary half-pour of sparkling wine. And there is plenty to peruse while the staff buses and cleans your spot. While you wait, check out the retail selection of wines and cheeses, with customized cards pointing out staff recommendations.

No matter who your server is, feel free to test their knowledge by firing off as many questions as you can. Trust us, they’ll ace them. Whether you’re a total wine-o or consider Franzia a gift from the wine gods, the staff is fully equipped to point you in the right direction to a wine you’ll love from their all-natural selection.

As far as the menu goes, the food rotates on a seasonal basis, so you know it’ll be fresh. But the star of the show stays on the menu year-round: the fried goat cheese curds. Yep, they’re exactly as decadent and indulgent as they sound. A sweet sauce and chives accompany the appetizer’s crisp exterior and pillowy interior, and the entire state of Wisconsin would either call it blasphemy or a revolutionary innovation.

The seasonal entrees and small plates don’t disappoint, either. If you’re not cheesed out by the curds, ask your server for a recommendation for a classic artisan charcuterie board.

2. Comedy @ The Den Theatre

Once you’ve sipped and nibbled your way through All Together Now, catch the Damen bus or an Uber to The Den Theatre on Milwaukee Avenue in the heart of Wicker Park.

An open lobby and classic box office greet you, and comedians with upcoming shows smile down at you from posters on the walls. Reminiscent of a fancy hotel bar, you can grab a drink at the downstairs bar while waiting for your show or head upstairs to another cozy bar option. There, you can sink into the soft, inviting sofas and chat with staff, friends, or other comedy-goers before doors open.

The Den, around since 2010, offers a range of shows from improv-style shenanigans to stand-up sets by relatively well-known comics. The range of shows runs the gamut, and the theater’s website provides brief descriptions of each, so research before picking a ticket. Some shows often sell out, and others have age restrictions, so it’s a good idea to book online in advance.

Whether your show follows more of a classic stand-up trajectory, a sometimes-cringey improv progression, or a musical set that relies heavily on shock factor, you won’t leave without at least a giggle or two.

3. Drinks @ Little Victories

Well, it’s time to top off the night with a drink or two. Leaving the Den, head northwest on Milwaukee Avenue and follow Wood Street toward Division Street. You might hear Little Victories before you see it.

Situated on the bustling Division Street, Little Victories is busy with 20- and 30-somethings having a cocktail in the lively yet relaxed space. Scanning the crowd, you may think to yourself, “Ohhh, so this is where all the not-quite-college-kids but not-quite-parents go out.”

A U-shaped bar decorated with the only bright lights in the place and a wide array of plants hosts bartenders showing off their skills and leaning in to hear orders over the rumble of the crowd. But don’t get us wrong, it’s not too loud. Remember, it’s not a college bar.

A green-and-white light fixture hangs above a pool table, and if you’re lucky, you’ll garner a crowd of observers. Near the back of the room, a few dart boards offer another option to fuel your competitive spirit.

The bar is one of those spots that seems to have found its niche: it’s a cocktail bar, but not too stuffy or fancy that you’ll feel out of place if you don’t know the difference between sweet and dry vermouth. It’s busy, but not so much so that it’s impossible to find a seat or walk through the room without strangers elbowing your drink out of your hand.

The drinks themselves are lovely. A specialty cocktail menu covers all the bases any good bar should. The “Madras Margarita” puts a spin on a classic mezcal margarita that works well. For another mezcal option, try the “Two Byrds One Stone,” which includes black lime-infused tequila, mezcal, chile liqueur, guava and lime. Not into mezcal or tequila? Don’t worry, the cocktail menu includes bourbon, vodka and rum options as well.

If you’re looking to keep the night going a little longer, consider an espresso martini shot for $6. Other house shots, including the ever-popular green tea shots you can’t really seem to escape, are also listed for $6.

Things to note:
– Little Victories does not accept reservations.
– Happy hours and daily specials are listed on its website.