Definitive Chicago Thread / Guide

TWO separate posts for character limit.

TLDR for most, so just scroll through the sections and find what you’re looking for. This is worth it, though, because there are a decent number of repetitive questions.

Know we have a couple other Chicago homies on the board, so let me know if you’d like to add anything. I can’t cover the whole city myself!

Quick Background

Chicago has 77 Community Areas and closing on 250 neighborhoods within those Areas. For example, Wrigleyville is a neighborhood in Lake View and Wicker Park is a neighborhood in West Town. No one really takes the time to make that formal distinction – everything is just a “neighborhood.” Those couple numbers, however, really highlight how neighborhood-centric Chicago is. You can see it just by looking at the CTA “L” map. Everything meets in The Loop and moves back into the neighborhoods.

While the immediate downtown areas has most of the tourist attractions, neighorhoods are the lifeblood of Chicago – it’s where almost the entirety of the city’s population lives, eats, drinks, etc. I understand a weekend trip makes it tough to explore, but I encourage you to venture outside The Loop and River North. I promise, it’s not a daunting commute – Blue Line to Logan Square and Red Line to Lincoln Park are less than 15 minutes from The Loop.

Chicago is an extremely clean city. Streets are well-maintained and you, likely, will not see a single homeless encampment.

Places to Stay

Greatest concentration of hotels across is The Loop and River North. Staying smack in the middle of The Loop can feel a bit desolate after the 9-5 because a lot of businesses close early. The city is making a concerted effort to make The Loop livelier after working hours. My recommendation is finding a hotel along E Wacker (e.g. 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 a few other considerations:

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

Public Transportation

Use it! Behind New York, Chicago has the most convenient public transit systems in the country. Google Maps is your best friend – all routes are 100% accurate, but download Transit Stop app for specific bus/train times.
Contactless payment on your phone or card is available at any turnstile. However, unlimited passes can also be bought at any Ventra machine (or their app).

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

I’m not going to dive into safety a whole lot, but visitors are almost never going to be taking the Red Line south of Sox-35th or Blue Line west of Clinton. Honestly, as along as you aren’t jumping on a train while drunk at bar close (2am – 4am), I wouldn’t spend much time extending safety past normal, city precautions. Personally, I take the Blue Line almost every day and have not once feared for my safety. You never want to speak in absolutes, though, and may still encounter a smoker, homeless, etc.

Sports!

Goes without saying – Chicago is a big sports town!

Both baseball parks are accessible on the Red Line. Get off at Sox-35th for Guaranteed Rate and Addison for Wrigley. Far more pregame / drinking options around Wrigley, 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 transit, it’s a decent enough walk to be annoying. Tailgate in a lot near Soldier Field or hit a couple bars in South Loop.

United Center is an easy run via Madison 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. Some bars walking distance from the UC, but you can also hang out in West Loop.

With respect to college sports, Chicago is a melting pot of B1G alumni, which makes CFB weekends very, very fun. If you want to check out a team bar, visit that university’s alumni website. As a Wisconsin alumnus, for example, Will’s in Lake View is our most well-known bar but Lottie’s in Bucktown is a fun time, as well.

Craft Beer and Breweries

Chicagoland (includes suburbs) nears 200 breweries, including ~70 inside city limits. There’s a lot to unpack with those numbers, so a few recommendations in the city itself: Hop Butcher, Maplewood, Goose Island, Half Acre, Dovetail, Revolution, Off Color, Guinness, Moody Tongue, Marz, Monochrome, Begyle, Solemn Oath, Burning Bush, and Begyle.

We have some fantastic craft beer bars and bottle shops, as well, including Hopleaf, Bangers & Lace, Beermiscuous, Bitter Pops, The Beer Temple, Village Tap, Centennial Crafted Beer, The Green Lady, and Map Room. My favorite? Hopleaf – awesome atmosphere, great neighborhood, and fantastic Belgian-inspired food.

Outside city limits, Brothership, Phase Three, MoRE, and Mikerphone all worth visiting.

Cocktail Bars

So many damn cocktail bars in Chicago… I won’t even scratch the surface of what’s out there, but Logan Square is the best cocktail bar neighborhood.

Personal favorites: The Meadowlark, Best Intentions, Queen Mary, The Alderman, Osito’s Tap, Kumiko, Nine Bar, Sparrow, Booze Box, Cara Cara Club, The Office, Lemon, Sportsman’s Club, Gilt Bar / The Library, and Friends of Friends.

Others: The Victor Bar, Arbella, TRUCE, Three Dots, Lazy Bird, Bisous, Billy Sunday, Scofflaw, The Whistler, Heavy Feather, La Pharmacie, Larry’s, The Hi-Lo, California Clipper, Dorian’s, Marty's Martini Bar, Blue Line Lounge, Gus' Sip & Dip, Lulu's, Double Fun, Valedor, Punch House, The Pearl Club, La Licor, Press Room, After, Matchbox, Golden Years, Nightcap, and Clara.

As I said, countless more but this should be a plenty good start.

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Patio Bars, Rooftops, and Day Drinking

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Chicago has a great nightlife, but day drinking reigns supreme, especially in the summertime.

If you're closer to River North and The Loop, take a stroll along the Riverwalk and stop at Tiny Tapp, The Northman, or Island Party Hut. There are a couple nice rooftops in the general area, as well, including LondonHouse, Cindy's, IO Godfrey.

Chicago's Lakefront Trail is 19 miles, which makes for an incredible recreation opportunity. If you want to take a couple bikes, though, consider stopping Shore Club at North Ave Beach or (a personal favorite) The Dock at Montrose Beach.

Some of my favorite neighborhood rooftop bars are J. Parker, Solana / The Up Room, Kennedy Rooftop, Gene's Sausage Shop, and Arriba.

For general patio bars, check out Happy Camper, Paradise Park, Recess, Kaiser Tiger, Pilsen Yards, Kirkwood, Barcocina, Central Park Bar, Sheffield's, Rogers Park Social, Cody's Public House, and SUNNYGUN. Number of breweries have patios, too, including Half Acre, Maplewood, Suncatcher, Goose Island (Salt Shed), Lake Effect, Dovetail, Begyle, etc.