CHICAGO

Chicago often gets a bad rap for the cold winter winds and safety concerns but it’s actually a world class city that remains relatively affordable compared to other cities of its similar size (NYC, LA). It’s the 3rd largest city in the US and was the 2nd largest for much of modern U.S. history from roughly 1890 until 1982. Accordingly, there is plenty to see and do around the city with major sights such as the Art Institute of Chicago and the Museum of Science and Industry housed in buildings from the 1890s (with more recent expansions of course). Without further ado:

West Loop:

  • As the trendiest fine dining neighborhood in the city, there are many options. My three favorites below.

  • Gaijin, an okonomiyaki restaurant (Japanese savory pancake) and one of my favorite spots in the city, provides a relatively niche food at a high quality for a decent price in one of Chicago’s more expensive areas. I’d suggest getting one each of the Osaka and Hiroshima style to try and if you have room for dessert, a kakigori (shaved ice). Reserve on Resy to guarantee a seat, although they do often have space for walk ins.

  • The Aviary is my favorite bar in Chicago and one of my top bars worldwide. It is definitely an experience and the prices reflect that, but at around $25 per drink (the standard cost of a cocktail in Chicago is $18-$20), it ends up being a bargain, especially since they serve on the stronger side of things. Top drinks include the Gumshopp Fizz, WASSUH bae?, Charred Pour Cornography, Do You Have To Let It Linger, Jungle Bird, In The Rocks, and Hermoso, although the menu changes every couple months. The 3-course drink tasting menu is a great way to go, but you can also order a la carte. You should really try to reserve on Tock ahead of time, but they do technically accept walk ins. This pairs well with dinner beforehand at Gaijin. I’d allow about 1.5-2 hours between the Gajin reservation start and the time you pick at the Aviary.

  • Aba … Reserve on OpenTable or Tock.

Pilsen:

  • Start at Panaderia Nuevo Leon, a bakery I found on Happy Cow (vegan Yelp). They have vegan conchas and other baked goods as well as plenty of non-vegan options. They sell some amazing tortillas of numerous flavors and will occasionally offer pozole. When they do, you need to try that, but it does have some meat in it.

  • After getting some sweets, head over to Fiesta Tamaleria el Barrio for my favorite tamales. The beans tamale might be vegan but is at least vegetarian. I also get a cheese & pepper tamale but they do offer some meat ones. Their drinks are a highlight as well. The Atole de Camote (sweet potato) is my favorite. Get this to go and take it across the street to enjoy in Harrison Park.

  • Once you’ve finished eating your tamales, walk next door to the National Museum of Mexican Art. The museum is entirely free and is one of my favorite museums in the whole world. I think it is the perfect size to visit without getting museum fatigue and still has enough depth to satisfy on repeat visits. The massive bead on beeswax mural in the second room is a must see.

  • If you are lucky enough to have worked up an appetite again while at the museum, head back towards the bakery for a sit down meal at 5 Rabanitos Restaurante & Taqueria. They have a strong offering of vegetarian dishes in addition to the meat plates and can probably be made vegan by asking for them without the cheese.

Misc:

  • Xi’an Cuisine - flatbreads (cumin lamb, tofu noodle) or biang biang noodles

  • Sun Wah BBQ has the best Hong Kong Style Chinese Barbecue in Chicago. Call ahead and reserve a duck dinner, which serves 4 and includes pieces of duck, duck fried rice, and duck soup. I recommend ordering some extra steamed buns.

  • Taco Maya - Chicagoland Indian-Mexican fusion that is open late and has good prices. They also give free chips and a salsa bar and have $1 samosa tacos on Mondays. My favorite tacos are the paneer, vegan chorizo, and hot Nashville cauliflower.