Stop for Some Chicago Goodness

Chicago is the best. I love finding worthwhile watering holes and hitting up the classics. I’m really into trying new places too, so suggest something to me on the right or at the bottom of this page. In return check out the Hot Spots I’ve been to recently, below, and I even made a nice “Everything a Visitor Needs to Know” guide to give to that cousin or college buddy who’s visiting/ asking “what should I do” so you didn’t have to. If you want to use Google almost exclusively (which you should 100% rely on a lot), then just see the Chicago highlights I recommend below.  

I also have a bunch of links at the bottom dedicated to helping people better understand Chicago. Goes without saying, but although I take the Red Line to work, I never miss an opportunity to ride The Other Line and the below is how I usually do it. And while you’re here, get your Chicago inspired gear made by the TOL team HERE.

Hot Spots

BiXi Beer – Logan Square – $40 Opened in mid-2018, this is a must hit foodie spot. Although they may not have the best beers in Chicago, they certainly provide a great dining atmosphere and absolutely amazing “new age” chinese food. The service and timing of each meal is impeccable and you feel like you should be paying a lot more. I’d keep this one on my radar, because I have a feeling it’s going to become much more popular than it already is. What you should get: Flight to try their beers (if not, Unspoken Rule), Lamb Wonton and Cripy Pork Belly Adobo.

Lan’s – Oldtown – $60 You’ve heard about it and thought, I don’t know if I’d enjoy that. Well if you like fun and alcohol, this is the place for you. With no holds barred, every rumor to be confirmed, Lan’s and its owner (Lan?) gives a let-loose environment that fosters more free trade than capitalism. You’ll be passing bottles of Tito’s vodka while singing Take Me Home County Road before you’re done with your last course and the whole time you’ll be thinking, why did I even question coming here. When Lan forces a bottle down you’re throat, you’ll remember the answer to that question. But all in all, so long as you know what you’re getting yourself into, you’ll have a great time. And the food definitely isn’t as bad as the yelp review will lead to you to believe. Come with a big group.

Reggies Rock Club – Southloop – $30 – A true southside staple where the likes of the Blue Brothers (would have) and that band you’ve never heard of have played. A truly unique venue with attached multi-level bar and a pretty sick rooftop. Word on the street is that the middle floor is getting licensed for a full bar as well. In a single night you might hear live bands consisting of metal, rap and indie music. You may even walk away with a new band to follow, but you will definitely not walk away disappointed. A place worth checking out ten times out of ten so make some time to check it. out. 

If you don't already know. Get these, Do these.

Deep Dish – Lou Malnati’s

Chicago Dog – Weiner Circle

Rooftop Bar – The J Parker Rooftop

Comedy Club – The Annoyance Theatre

Neighborhood Walk – Milwaukee Ave. walk through Wicker Park

Brewery – Lagunitas Brewery

Cigar Bar – UpDown Cigar Shop 

Chi Restaurant – BiXi Beer


And pick a neighborhood and do things in it

Wicker Park –  Coolest, hippest, area with shopping and quality restaurants and bars.

Logan Square – Probably the second coolest, hipperst area with less shopping, fewer restaurants.

East Lakeview – Where a lot of young people live. Dotted with great restaurants and fun bars. Home to Wrigleyville and Boystown.

Lincoln Park – Nice neighborhood blocks, dotted with great restaurants and fun bars. Home to Lincoln Park and it’s zoo/conservatory.

West Loop – Eat and drink the best of the best here. Where’d you should take a date to make a good impression.

River North – Probably where you’d take your parents to show them how nice Chicago is. Home to the Magnificent Mile shopping.

Old Town – Probably where you’d go for after-dinner drinks on your own to not stray too far from your family. 

The Loop – Home of big buildings, the River Walk, and the Bean – right by Navy Pier.

Other Hoods Worth Making a Prolonged Stop – China Town, Lincoln Square, Pilsen, Andersonville, North Center, Uptown, Bucktown.

Need a bar?

For your brewery uber-crawl, West Loop (with optional Northside start): Half Acre Beer Company, Dovetail Brewery, Begyle Brewing Company, Metropolitan Brewery, [WEST LOOP START] On Tour Brewing Company, Goose Island Beer Company, and Great Central Brewing Company. 

For your yuppie bar crawl, Old Town: Old Town Pour House, Happy Camper, Benchmark, Suite Lounge, The Vig Chicago.

For your college-days bar crawl, Wriggleyville: Sluggers, Cubby Bear, Old Crow Smokehouse, Country Club, The Graystone Tavern, Underground Lounge, Yakzies Bar and Grill, Smartbar.

For your hipster/dive bar crawl, Wicker Park: Bangers & Lace, Goldstar, Phyllis’ Musical Inn, Easy Bar, Fatpour Tap Works, Rainbo Club, Queen Mary, Map Room.

For your alternative hipster bar crawl, Logan Square: The Whistler, Emporium Logan Square, The Heavy Feather, Slippery Slope, East Room, The Boiler Room, Scofflaw, Best Intentions.

For your back to college-rage bar crawl, Lincoln Park: Lion’s Head, Tobacco Room, The Apartment, Max Bamboo Lounge, Halligan’s Bar. 

For your dive bar crawl, Bucktown: Tap Room, Corner Bar, Web Pub, Danny’s Chaleston, O’s Tap, Gallery Cabaret, Map Room, Jean & Ed’s, Lottie’s.

Clubs, clubs, clubs, River North: Bottled Blonde Chicago, El Hefe Chicago,  Prysm, Smartbar, Spybar, The Mid, Underground Chicago

Blues and Jazz clubs: Kingston Mines, Green Mill Tavern, B.L.U.E.S.


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