The Number 1 Drinking City in the USA

A big question at the top of everyone’s list when they are traveling to a new place is “Where can I grab a drink and have a fun time?” Well we have that answer for you and much much more with the following city: Chicago

Chicago offers much of the same entertainment and attractions as NYC but is nicer, cheaper, and easier to navigate. It was rated the #1 city to drink in by GQ and its variety of neighborhoods have a little culture for every type of person. No matter how much you want to spend, there are tricks to expand your budget and deals around every corner.

Although it can cost more to travel to in the summer, this city is SO much more enjoyable in the months between May and September. That’s about the time the locals come out of hibernation and all of the community events start.

Below are some lesser known things to do in Chicago that will give you flexibility with your spending.

Things to do:

(Bringing your own alcohol to any of these places is prohibited so don’t get caught 😉 )

Festivals

In the summer there are countless festivals throughout the city offering variety of food, beer, music, and entertainment. Festival topics range from art, to food, to culture and heritage, and also recognizing the spirit of communities in the area. Almost every neighborhood puts on a summer festival showcasing popular restaurants and stores found within. Many are free or for a small donation.

There are also lots of activities in the parks in summer months such as nightly movies played on inflatable big screens. There is also regular music at the amphitheater at Millennium Park. Make sure to bring a blanket and some snacks.

America’s Oldest Sport-Baseball

Going to baseball games are cheap and a nice way to spend an afternoon in the sun. The White Sox are part of the American League and they are located on the South Side of Chicago (still in a safe neighborhood). Tickets are as cheap as $7. The Chicago Cubs are part of the National League and are located in Wrigleyville on the North Side. Both stadiums are within walking distance of the Red Line Trolley.

Beaches

Chicago sits on the shores of Lake Michigan, which means there’s beach and it is free. Go to Oak Street Park for sun bathing (closest to downtown), or North Avenue Beach for some pick up games of beach volleyball (sometimes there are tournaments going on this beach, but there are always courts open on the north end). There is a building on this beach that looks like a docked ship. The bottom has public bathrooms, net and volleyball rentals, and a small cafe. The top half is a restaurant called Castaways. You can also do stand up paddle boarding (SUP) and JetLev at this location. Both of these beaches are popular so if you don’t like crowds you can take a cab to Montrose Beach, but it is quite a bit farther north. Note – all Chicago beaches require swimsuits, so girls you will be asked to put a shirt on, if you try going topless.

Museums

Museums offer a free day once a week if you give them a local address. If you want more time at the museum and have a little more to splurge, get a multi-attraction ticket.

The Lincoln Park Zoo

The Zoo is free everyday but I wouldn’t recommend it. I personally don’t believe in zoos, but this one seems especially sad as most of the animals live in cages that seem too small for the animals to be happy.

Navy Pier

The pier does a firework show every Wednesday and Saturday night in the summer. Catch a free trolley by the Grand stop on the Red Line in River North. The pier is mostly a tourist destination but the Ferris wheel located there is a nice way to relax. (The Ferris Wheel is also known as the Chicago Wheel because the first one opened to the public opened in June 21, 1893 here in Chicago for the World’s Columbian Exposition.)

For more on what’s happening in the city, check out our local commuter paper The Red Eye which covers local events for the coming week.

Food & Booze

While most meals will cost between $8.00 and $20.00 at a restaurant (including tip which should range from 15%-20% of your overall check or $1 per drink at the bar), there are many places offering weekly deals such as $1 tacos at Lincoln Station in the Lincoln Park neighborhood. Search for some of these if your food budget is a concern.

When you move north from downtown into the residential neighborhoods, there are many BYOB (Bring Your Own Beer) restaurants. These restaurants don’t serve their own drinks, but allow you to bring your own alcohol. There is a cork fee (a tax added to your bill to drink at the restaurant) at some of these restaurants, but others are completely free. Buying a bottle of alcohol at the store and bringing it with you is far cheaper than ordering drinks one by one. Grocery stores generally sell the cheapest alcohol. Local grocers are Jewel-Osco, Wal-Mart, Trader Joes, and Target. For a broader selection or for later hours you can try liquor stores (off-license) which are found in every neighborhood.

Getting Around:

The cheapest way to get around is the CTA- the local train (the “L” or Trolley) and bus routes. Buy a 3-day Ventra pass for $20 or a 7 day Ventra pass for $28. You can also purchase a card for $5 and load it with money as you go. These passes give you unlimited rides on both the L and buses. Although buses make it easier to navigate the city East/West, they run infrequently and can be really frustrating. The best bus for tourists is the 151. It runs slow, but makes a number of stops throughout downtown and up north including Union Station, the Art Institute and Millennium Park, the John Hancock building, North Ave beach, and Lincoln Park Zoo.

For the train, The Red Line and Blue Line run 24 hours a day, 7 days a week and will take you anywhere you would likely go in the city. The Blue Line runs directly from O’Hare to downtown, and the Orange Line runs from Midway to the Loop where it connects to Red. Union Station, Megabus and Grey Hound stops are all within walking distance of the Quincy Brown Line stop. Cabs/Ubers from the airport range from $30-$60 to get downtown and can take 3x as long during rush hour so I suggest taking the train even if you think it is dirtier.

I have always had good luck with cabs. Most of the places in the areas you will visit will take less than 20 mins to get to (not during rush hour) and will cost between $8-$25 including tip.

Neighborhoods

Everything you will likely want to do will be between the Sox-35th stop and Addison stop on the Red Line, and the California stop and the La Salle stop on the Blue Line. Neighborhoods along these routes are listed below.

Wrigleyville is a young neighborhood. Many people move here from out of state after college so it is very popular for people who are 21-24 although there are a variety of people in this neighborhood before and after Cubs games. It is a party neighborhood and very busy on the weekends. Clark Street, right outside the stadium, is lined with bars.

Lakeview is mostly residential although there are quite a few bars, restaurants and shops on Broadway and Halsted streets. Halsted street is the main strip for Boys Town, the gay friendly area of Chicago with lots of gay bars and clubs. Keep a close eye on your drink and wallet here late at night, but this neighborhood is mostly safe.

Lincoln Park is mostly residential and family oriented. Lincoln Street is the bar street of this neighborhood for all ages although some of the dive bars cater to the DePaul students whose campus is nearby.

Old Town is sort of where late 20’s/early 30’s go once outgrowing Wrigleyville. There’s a variety of types of restaurants, bars, and comedy clubs in this neighborhood including the nationally known improv theater The Second City with shows around $12. Improv shows are a staple in Chicago and can be found for cheap in almost every neighborhood.

River North is popular for happy hour after work and easy to access for tourists as many hotels are located here. It’s near Navy Pier and the Magnificent Mile. Most of Chicago’s most well known nightclubs are also located in this neighborhood as well as many restaurants and stores.

The Loop is the area in the middle of the square that is created by the elevated ‘L’ tracks. This area is pretty dead on the weekends and after work hours. Sometimes the stores on State Street can be less crowded than the ones on the Magnificent Mile if you want to do some shopping. Once you see the Sears Tower aka Willis Tower, there’s not a lot to do in the area. Head north to River North.

West Loop is an “up and coming” neighborhood. This used to be the meat-packing district and was quite industrial, but many of the old building are being converted into restaurants and condos. Google bought a large property here and the Real-World house can also be located in this area. Besides some well-known restaurants, there’s really no reason to venture over there. Some of the restaurants are overpriced, and many of them have a long wait.

Wicker Park/Bucktown are know as the “hipster” neighborhoods. If you like craft beer, flannel shirts, and thick-rim glasses, this is the neighborhood for you. I have spent less time in the neighborhoods along the blue line. The stops between the Loop and the Division stop have excellent food but are a little more expensive. Once you get to the Damen and Western stop, the prices are more reasonable. There are TONS of restaurants and shops right off of both of these.

So there you have it, Chicago in a nutshell- Go in the summer, buy some drinks on the cheap, and have fun exploring the cities abundance of affordable activities!