Definitive Chicago Thread / Guide

TWO separate posts for character limit.

Quick Background

Chicago has 77 Community Areas and near 250 neighborhoods. Technically, neighborhoods exist within Community Area. For example, Wrigleyville is a neighborhood within Lake View and Wicker Park is a neighborhood within West Town. Few people make the distinction.

This underscores how neighborhood-focused Chicago is. You can see it on the CTA “L” map: every rail line converges in The Loop before branching back out into the city’s neighborhoods.

While downtown is home to many famous attractions, neighborhoods are the true heart of the city. They’re where most Chicagoans live, dine, and socialize. If visiting for only a weekend, it's tempting to stay within The Loop and River North, but I’d encourage you to explore beyond downtown. It’s easier than you think—Logan Square is less than 15 minutes from The Loop via the Blue Line, and Lincoln Park is just a short ride north on the Red Line.

Chicago is remarkably clean for a city of its size.

Places to Stay

Highest concentration of hotels is in The Loop and River North. While staying in the The Loop puts you close to major attractions, it can feel quiet after business hours since many offices and businesses close in the evening. The city has been working to bring more nightlife and dining options to the neighborhood, but it's so heavily concentrated to the 9-5 workforce.

For most visitors I recommend staying in one of the following areas: E. Wacker (e.g., Hyatt Regency Chicago), S Michigan overlooking Millennium and Grant Parks (e.g., Chicago Athletic Association), and River North, which offers a great mix of restaurants, nightlife, and walkability (e.g., The Westin Chicago River North).

Hotels are less common in residential neighborhoods, but a few alternatives include:

West Loop is home to upscale hotels such as Nobu Hotel and The Hoxton. If dining is a priority, this neighborhood places you in the center of Chicago’s renowned restaurant scene.

For a more local feel, consider Hotel Lincoln in Lincoln Park, The Robey in Wicker Park, or Hotel Zachary in Wrigleyville.

McCormick Place is a convention center with substantial hotel inventory nearby. While convenient for conference attendees, it’s not the best choice for leisure travelers looking to explore the city.

Public Transportation

After New York City, Chicago boasts one of the most extensive and convenient public transit systems in the country. Google Maps is reliable for routes, but the Transit Stop app is best for real-time bus and train arrival information.

Riders can pay with a contactless credit card, debit card, or mobile wallet at any CTA turnstile. For those using transit frequently, unlimited-ride passes can be purchased through the Ventra app or at vending machines throughout the system.

The Blue and Orange Lines provide direct service to ORD and MDW, respectively. The Blue Line, in particular, has become one of the CTA’s busiest routes as neighborhoods on the city’s Northwest Side—such as Avondale, Bucktown, Logan Square, and Wicker Park—have continued to grow in popularity.

As for safety, most visitors will find the CTA no different from transit systems in other major cities. Standard urban awareness goes a long way. While late-night travel may require extra caution, the vast majority of rides are uneventful. I ride the Blue Line regularly and have never felt unsafe. That said, as with most large transit system outside Asia, you may occasionally encounter disruptive behavior, etc. Staying aware of your surroundings and using common sense is generally all that’s needed for a comfortable experience.

Sports!

Chicago is a sports town through and through.

Both MLB stadiums are easily accessible via the CTA Red Line - Sox–35th for Guaranteed Rate Field and Addison for Wrigley Field. Wrigleyville offers a much larger selection of bars and restaurants. Guaranteed Rate Field, on the other hand, delivers a classic tailgating experience.

While public transit can get you close to Soldier Field, there’s still enough of a walk to make it somewhat cumbersome. Most fans tailgate in lots surrounding the stadium or start at a bar in nearby South Loop.

The United Center is easy to reach via the Madison bus or the newer Green Line station at Damen. While the immediate area is still developing, plans are underway that will transform the neighborhood. There are a handful of bars within walking distance of the arena, but many fans prefer to spend time in the West Loop before heading over.

College sports also have a strong presence in Chicago. As a hub for Big Ten alumni, the city comes alive during CFB. Most universities maintain designated alumni bars throughout the city. As a Wisconsin alumnus, I can vouch for Will’s Northwoods Inn in Lakeview, while Lottie’s Pub in Bucktown is another great spot to catch a game.

Craft Beer and Breweries

Chicagoland—including the suburbs—is home to nearly 200 breweries, with roughly 70 located within Chicago city limits alone. With so many options, can be tough to know where to start, but some standout breweries include Hop Butcher, Maplewood, Goose Island, Half Acre, Dovetail, Revolution, Off Color, Guinness Open Gate, Moody Tongue, Marz, Monochrome, Begyle, Solemn Oath, and Burning Bush.

Chicago also boasts an exceptional craft beer bar and bottle shop scene. Favorites include Hopleaf, Bangers & Lace, Beermiscuous, Bitter Pops, The Beer Temple, Village Tap, Centennial Crafted Beer, The Green Lady, and Map Room. If I had to pick one, Hopleaf gets my vote - great atmosphere, neighborhood setting, and a Belgian-inspired food menu.

For those willing to venture beyond the city, Brothership, Phase Three, More Brewing, and Mikerphone are well worth the trip.

Cocktail Bars

Chicago has an absurd number of great cocktail bars - so many that there’s no way to cover them all. If you’re looking for the city’s strongest concentration of cocktail spots, Logan Square gets my vote.

My favorites: The Meadowlark, Gus' Sip & Dip, Kumiko, Best Intentions, Queen Mary, The Alderman, Osito's Tap, Nine Bar, Sparrow, Booze Box, Cara Cara Club, Sportsman's Club, Gilt Bar / The Library, and Friends of Friends.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, Bar Bambi, and Friends of Friends.

Also worth checking out: The Victor Bar, Arbella, TRUCE, Three Dots and a Dash / The Bamboo Room, 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, Lulu’s, Double Fun, Valedor, Punch House, The Pearl Club, La Licor, Press Room, After, Matchbox, Golden Years, Nightcap, Bar Sotano, and Clara.

Chicago’s cocktail scene runs deep, but this list should give you a very solid place to start.

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Patio Bars, Rooftops, and Day Drinking

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Chicago is known for its vibrant nightlife, but in the summer, day drinking is arguably the city's favorite pastime.

If you're staying near River North or the Loop, spend time along the Riverwalk and grab a drink at Tiny Tapp, The Northman, or Island Party Hut. The area is also home to several excellent rooftop bars, including LondonHouse, Cindy's, and IO Godfrey. Neighborhood rooftop options include J. Parker, Solana and The Up Room, Kennedy Rooftop, and Gene's Sausage Shop.

For a more active outing, take advantage of the 19-mile Lakefront Trail. If you're biking along the lake, make a pit stop at Shore Club on North Avenue Beach or, for a more laid-back vibe, The Dock at Montrose Beach, a personal favorite.

If patios are more your style, Chicago has plenty of great choices.