6 Casual Date Spots In West Town, Chicago

West Town is the area between the West Loop and Humboldt Park.

Facebook Charlaton Chicago restaurant bar

Photo: Facebook/Charlaton Chicago

Like a successfully landed pick up line, the perfect date spot is one in a million. My personal preferences lean towards low-key, cozy bars and restaurants that feel simultaneously hidden and happening. Since this article will provide a list of my favorite places to play coy and bat my eyelashes in Chicago’s West Town – which I will semi-inaccurately define as the area between the West Loop and Humboldt Park – I feel it is only fair that I let you know the qualities I seek in a courtship locale, as they may be different than yours.

For me, a promising evening of confusing banter and sexual tension requires the following:

  1. A proper noise level, meaning I can hear the person I’m unconditionally smiling at and dip should they go into detail about their increasing stock portfolio.
  2. Accessible booze – either booze you can buy or booze you can bring.
  3. Convenient location with easy access to other places (bars, shows, public transit, people) to avoid a stale date or the I-want-to-go-home-but-I’m-trapped disaster.

Everything else is negotiable, but the following restaurants and bars nail those three like a third-date special.

1. Charlatan

1329 W. Chicago Ave

Charlatan is perfect for a date you want to impress. They’ve got a killer menu that puts an inventive spin on Italian dishes, which you can be conservative with (the best bruchetta you’ve ever had for $10) or go balls-out with (pigs head for two, $55). The same goes for the drink menu, which offers a $3 Hamms for slim wallets seeking the ambiance, and well-crafted cocktails for the slow sippers at $10. Try my personal favorite, the Dehumanizer, a standout mix of George Dickel Rye, Botran Reserva, Amaro Montenegro, grapefruit, and bitters.

Facebook Charlatan Chicago bar
Photo: Facebook/Charlatan Chicago

2. Silver Palm

768 N Milwaukee

The Silver Palm is quirky and unforgettable from the second you spot its trademark silver railroad car. Have dinner in the railroad car, or hang out at the always-busy bar, aptly named The Matchbox. The Matchbox is a Chicago institution, a side-step-narrow bar that’s always crowded, but that’s part of its charm. Use the excuse to talk close and be adventurous when picking your cocktail. For $9.50 you’ll get a dynamic drink that sometimes comes with an extra carafe. Try the gin and jam.

Facebook The Silver Palm Chicago bar
Photo: Facebook/The Silver Palm

3. City Winery

1200 W Randolph Street

For an upscale date that you’re willing to invest in, City Winery offers everything you need. Concert, check. Dinner, check. Wine tasting, check. The concert venue is where you want to be – a room full of intimate tables where listeners eat dinner and drink wine as they enjoy the concert, just inches from the stage. If you need the one-two punch of date nights, I highly recommend this place.

3. city winery
Photo: Flickr/Georgia Hinaris

4. Innertown Pub

1935 W Thomas Street

For the low-key first date, the jukebox and dive ambiance will put you at ease. Innertown Pub’s modest from the outside, a hole-in-the-wall on a quiet street, but the inside is magic. There’s an old-time charm in the checkered floor, lit by antique lampshades and string lights. Sit at the tables on a platform a few yards away from the bar so you can hear one another talk. As the night goes on, the bar will fill up with locals and become electric. This pick is a good fit for those who want to play a game of pool and have a few intimate get-to-know-you beers.

4. Innertown pub
Photo: Flickr/Andy

5. Wasabi

2115 N Milwaukee

Be prepared to indulge in some serious ramen. There’s nothing better than getting to know someone over comfort food, and after fondling tender pieces of pork belly and soft-boiled egg, it will be hard not to leave a little closer. Try Wasabi’s Miso Ramen, a libido stroking combination of egg noodle, rich pork broth, Berkshire pork belly, soft-boiled egg, marinated bamboo shoot, bean sprouts, sesame, and scallion for $13.

Facebook Wasabi Chicago
Photo: Facebook/Wasabi Chicago

6. Irazu

1865 N Milwaukee

Bring your own booze and prepare to be face-deep in Costa Rican heaven. Irazu’s vibe is very easy-going, with picnic benches situated outside the restaurant that are perfect for summer date night. Try the Pepito Sandwich, your choice of rib eye or chicken with sautéed onions, cheese, beans, and Lizano sauce. Beyond bangin’ for $7. There are no reservations on the weekend, so if you don’t get there early, prepare to wait. Then again – that’s why you brought your own booze.

7. Irazu
Photo: Flickr/PPoHio

Lena Kazer

Lena is a Chicago native, her travel style consists of red cowboy boots that make her feel like she can take over the world. She adores Peru and can't travel without her journal to draw or write in.

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