Definitive Chicago Thread / Guide

TWO separate posts for character limit. TLDR for most, so just scroll through the different sections and find what you're looking for. This is worth it, though, for the repetitive, annual questions that are asked on this board.

Got the idea from Abita, who did a similar thread with Boston. We see a lot of Chicago threads start to pop in spring/summer, so good time to get it started and answer any questions. I’ll periodically update with openings, closings, construction, etc.

Know there are a couple other current Chicago homies on the board, so let me know if you want to add anything. I definitely forgot stuff.

Quick Background

Chicago has 77 community areas and 200+ neighborhoods within those areas. For example, Wrigleyville is a neighborhood in Lake View and Wicker Park is a neighborhood in West Town. Less formally, no one really takes the time to make the distinction. Those numbers really highlight how neighborhood-centric Chicago is. You can see it by looking at the CTA “L” map. Everything meets in The Loop and moves back into the neighborhoods.

While the immediate downtown area has most of the tourist attractions, neighborhoods are the ‘lifeblood’ of Chicago. I understand a weekend trip makes it tough to explore much, but I encourage you to venture outside The Loop and River North.

Places to Stay

Greatest concentration of hotels—across all price ranges—is The Loop and River North. Staying smack in the middle of The Loop can feel a bit isolated after the 9-5 because a lot of businesses close early. My recommendation is to find a hotel along E Wacker (i.e. Hyatt Regency), S Michigan along Millennium / Grant Parks (i.e. Chicago Athletic Association), or anywhere in River North (i.e. Westin Chicago River North).

Hotels tend to be scarcer in neighborhoods, but some other considerations:

- West Loop has a few high-end hotels, including Nobu and The Hoxton, if price isn’t a big consideration. Plus, you’re in the center of Chicago’s biggest culinary neighborhood.
- If you really want to immerse yourself in a neighborhood, try for Hotel Lincoln in Lincoln Park, The Robey in Wicker Park, or Hotel Zachary in Wrigleyville.
- McCormick Place is a huge convention center that frequently hosts large conferences. Decent number of hotels down there, but wouldn’t recommend if you’re here for vacation.

Public Transportation

Cannot emphasize enough to utilize it! Chicago has one of the most convenient public transit systems in the country. Use Google Maps to your advantage – all routes are 100% accurate, but download Transit Stop app for specific bus/train times.

Unlimited passes are available at any Ventra vending machine. You can buy a card or load onto your contactless. It’s the cost-effective option if you’re planning to frequent public transit, otherwise feel free to use contactless / phone wallet at a turnstile.

Blue and Orange lines run direct to/from ORD and MDW, respectively. Blue Line has quickly become one of the busier runs in the city with population explosion on the city’s west side (i.e. Bucktown, Logan Square, Wicker Park).

I’m not going to dive into safety a whole lot, but weekend visitors are almost never going to be taking the Red Line south of Sox-35th or Blue Line west of Clinton. As long as you aren’t jumping on the train drunk at bar close, I wouldn’t spend much time extending safety past normal precautions. Personally, I take the Blue Line almost every day and have never feared for my safety. I always see people with suitcases going to/from ORD. I do the same unless work is paying, then I'll Lyft/Uber.

Sports!

Goes without saying – Chicago is a big sports town!

Both baseball parks are accessible via Red Line. Get off at Sox-35th for Guaranteed Rate and Addison for Wrigley. Far more pregame / drinking options around Wrigleyville, but still a fun tailgate atmosphere when the White Sox are home.

Soldier Field is a bit of a pain in the arse. Though not completely inconvenient from public transportation, a decent enough walk to be annoying. Tailgate in a lot near Soldier Field or hit a few bars in South Loop.

United Center is an easy run via bus or the new Green Line stop at Damen. Not much else to say, but the city will be developing the hell out of that area in the next several years. Plans look awesome.

Chicago is a melting pot of B1G alumni, which makes CFB football weekends very fun. If you want to check out a team bar, visit that university’s alumni website. As a Wisconsin alumnus, can tell you that Will’s in Lake View is the spot.

Craft Beer

Chicagoland nears 200 breweries, including ~70 inside city limits. There’s a lot to unpack with those numbers, so a few recommendations based on different styles:

- Best hazy IPA brewery is Hop Butcher for the World. They opened their taproom a few years in Half Acre’s old space in North Center.
- For traditional styles, Dovetail is a must-visit + walking distance from Hop Butcher.
- Goose Island is, obviously, the OG of BA stouts, so I’d encourage you to visit their Fulton taproom – great cellar list. They also re-opened the brewpub near Salt Shed, which is a nice setting along the river. I do like GI, but my favorite breweries for stouts are Maplewood (BA Cuppa) and Half Acre (Benthic). Revolution’s Deth series has a cult following that might be worth visiting, too.
- Funk and sours are a bit less for my palate, but Off Color is a nice space in Lincoln Park and Five Squared Pizza holds residence.
- With respect to large breweries, Guinness opened their second US brewery in West Loop just under two years ago. It’s a wonderful space in a great neighborhood.
- Moody Tongue is a brewery that has an accompanying restaurant with a Michelin star.
- Some of my favorite craft beer bars and bottle shops are Hopleaf, Bangers & Lace, Beermiscuous, Bitter Pops, The Beer Temple, Village Tap, Centennial Crafted Beer & Eatery, The Green Lady, and Map Room. My favorite of these? Hopleaf. In my opinion, best beer bar in the city and an incredible atmosphere.
- Other breweries in and around Chicago: Maplewood has a solid hazy offering, Solemn Oath has a location in Logan Square, Marz and Monochrome are worth visiting on the south side, Half Acre is one of the OG craft breweries in Chicago, and a few suburban breweries worth visiting are Brothership, Phase Three, MoRE, and Mikerphone.

Cocktail Bars

There are so many damn cocktail bars in Chicago. I won’t even scratch the surface of what’s out there, but I love going to The Meadowlark, Best Intentions, Queen Mary, The Alderman, Osito’s Tap, Kumiko, Nine Bar, Sparrow, Booze Box, and The Office.

Others I’ve been to / are known: The Victor Bar, TRUCE, Arbella, Three Dots and a Dash, Lazy Bird, Bisous, The Violet Hour, Billy Sunday, Scofflaw, Cara Cara Club, The Whistler, Heavy Feather, La Pharmacie, Larry’s (The Lawrence House), Sportsman’s Club, The Hi-Lo, California Clipper, Valedor, Punch House, The Pearl Club, and Matchbox.

100+ more, but this should be a good start.

Patio Bars, Rooftops, and Day Drinking: Happy Camper, Paradise Park, Cabana Club / The Up Room, J. Parker, Federales (Logan location because WL is ratchet), Recess, Kaiser Tiger, Pilsen Yards, Cindy’s, IO Godfrey, Utopian Tailgate, Shore Club (seasonal), Kirkwood, Barcocina, Park & Field, Welcome Back Lounge, Central Park Bar, Sheffield’s

Plenty others, including places I’ve mentioned throughout this thread (i.e. Parson’s).