Chi-City Life: A Local’s Guide To Chicago

Written by Stuart Cooke – Guest Contributor 

Are you thinking of going to the windy city but don’t know where to begin? We’ve put together a local’s guide to Chicago, covering all of the best bars, bites and favorite sights told to us by Chicago residents. 

Best time to go

First, things first, when is the best season to visit? Summer offers plenty to do in the city, with the festival season kicking off with Chicago Blues, the world’s largest free blues festival in June and the Taste of Chicago in July. The average daytime temperature in July is 28C so is something to consider if you’re not partial to city heat. March is another popular alternative when the city comes alive and the rivers run green for the St Patrick’s Day Parade. The average temperature is around 17C. If you fancy a chill, you can alternatively visit the city during the winter months but remember to wrap up with average temperatures for January just hitting 0C. 

Eats

Good food is the most important part of any holiday. I mean it’s okay to do nothing but eat junk food, you’ve worked all year for this! Overlook the standard haunts you’d hit and take a look at these places as recommended by Chicagoans. 

Sweet Mandy B’s, Lincoln Park

If you have a sweet tooth you need to get yourself to Sweet Mandy B’s. Indulge in cookies, cupcakes, brownies and breakfast bites at this neighborhood bakery. 

Dusek’s Board and Beer, Pilsen

After something more upscale? Dusek’s Board and Beer was awarded a Michelin Star in 2016 and is one of the best restaurants in Chicago. Enjoy a laid-back atmosphere and unbelievably creative recreations of traditional pub grub. If you’re looking to push the boat out, then this it it.

Al’s Italian Beef

Want to experience something you will only find in Chicago? Enter the Italian Beef Sandwich. Brought to Chicago in the 1930s by Italian immigrants, this Italian roll contains a delicious filling of sliced seasoned beef, peppers and jus. Al’s Italian Beef is now a chain, however, the joint on Taylor Street is the original that goes back to 1938. Still serving it how Mamma would have made it, there are no seats, so grab a napkin and eat it on the go. 

Cafe Central, Westown

For those of us who want to enjoy great food and a good price. Cafe Central is a family ran Puerto Rican BYO restaurant. You’ll feel right at home with your beer and Arroz y habichuelas. 

 

Drinks

Chicago is the city of the Speakeasy. Notorious for legendary Al Capone and his bootleggers, so if there’s a city you’ll enjoy some tipple in, it’s here. We’ve put together a few places recommended by locals that will suit every budget. 

Maria’s Packaged Goods

One of Chicago’s “slashies” which is a liquor store combined with a bar, where you can sip on a cocktail at the bar and grab a bottle of wine for the road. Often considered to be dive bars, Maria’s Packaged Goods in Bridgepoint, bucks the trend. Popular with artists and musicians, this place offers more than 500 varieties of beer and serves up Korean/Polish street food called Kimski. The ideal combination for a lazy night out that brings the party home. 

Empty Bottle 

If you’re into your rock history, you can’t pass up the Empty Bottle in the Ukrainian Village district. The venue has hosted bands from Arcade Fire to The White Stripes when they were up and coming artists. It does have a dive bar vibe but the kind that means you can shoot some pool, drink some pints and listen to good bands on a small stage who may just top the charts one day. 

The Hideout 

In an out-of-the-way industrial part of town inside a late 1800s-era house, this beloved local haunt has a small front bar and a back room performance space that hosts live bands, comedy acts, poetry open mics and late-night dance parties. If you’re in the city in September be sure to check out the Hideout Block Party to experience to truly experience this unique bar scene.

Reggies

The place to go for any punk fan, this iconic venue in South Loop is where to go. Boasting one of the best roof bars in the city complete with TVs, games and picnic tables. Enjoy live shows from punk and mental bands and the bar’s famous chicken sandwiches. And if you can’t face the cab home, don’t worry there are rooms at Reggie’s Hotel. 

 

Sights

16th Street Murals, Pilsen

If you love street art then you have to check out these murals in Pilsen. Enjoy the perfect backdrop for your Instagram snaps with street art from renowned artists around the world adorning gable walls. After all that strolling you might as well grab lunch. Well you’re in luck as Pilsen is also the best area in the city to get authentic Mexican cuisine. Go easy on the Mezcal! 

Humboldt Park

Many visitors overlook the parks, opting for the lakefront, but don’t make this mistake. Located on the West Side, Humboldt Park is the ideal place to lie out a blanket and kick back at the end of a day of sightseeing. Stroll amongst the lagoons, dine at the waterfront Boathouse Cafe or take a short urban hiking trail on an abandoned railway line that connects several of Chicago’s neighborhoods. The options are endless.

Montrose Beach

Chicago enjoys warm summers and the lakefront beaches are a popular spot to cool off in the city. The city’s buildings come up to the sand at places like Oak Street Beach but to get some peace away from the bustling streets venture further north and you’ll discover Montrose Beach, the city’s largest and the best-kept secret of Chicago locals. Unwind with volleyball, walk the birding trails and explore the sand dunes. Grab a refreshing cocktail and watch the sunset. This isn’t the Chicago they tell you about in the brochures! 

Garfield Park Conservatory

This beautiful conservatory is over a century old. When you walk in you are instantly met with the smell of fragrant flowers or you might just be lucky enough to enjoy a seasonal garden show. It is completely free to enter so definitely something to check out if you are into horticulture. 

Green City Market

There’s nothing better than an old-fashioned farmer’s market. Take in the day and stroll around local produce and tuck into some lunch on the go. This market is a popular place with locals and tourists alike and has been named one of the top ten farmer’s markets in America.

Graceland Cemetery, Wrigleyville

Okay, so some might find cemeteries a little bit morbid, but Graceland Cemetery is the ideal place to explore Chicago’s history. Everyone who was anyone in Chicago life is buried here. Enjoy a free self-guided cemetery, tour and marvel at the stone statues, tombs and mausoleums that reside in this park-like cemetery, which also doubles as an arboretum.  

 

Stay

Chicago offers so many different types of accommodation to call home. From luxurious to budget, there is something for everyone in this city. But instead of choosing the same old chain hotel, we’ve put together a few hotels recommended by locals for you to choose from.

Hotel EMC2, Magnificent Mile

If you’re after an eccentric hotel that will be an attraction in itself then look no further than Hotel EMC2. Modeled after, you guessed it, the famous scientist Albert Einstein, this hotel blends art and architecture all in one place. Within walking distance of Chicago’s main attractions and boasting rooms equipped with Amazon Echo’s this hotel has everything you need for a modern get away. 

Adeline’s Sea Moose, Lake Shore Drive 

If your budget has no limit, then why not stay in Chicago in style in this private yacht? Featuring an upper deck and plenty of cabin space below deck, it’s a quirky alternative to a hotel. You can also take the yacht for a cruise to take in the Chicago skyline, but of course you won’t be the one sailing it.  

Longman & Eagle

Longman & Eagle offers six boutique rooms above a restaurant in the neighborhood of Logan Square. Designed with retro touches, this is the ideal base to start exploring the city. And if you don’t fancy exploring the party district of Logan Square, you can just pop to the restaurant downstairs and try and pick which drink to have from over 400 types of whiskey. You might be there a while…

Hi Chicago! The Loop 

We know hostels aren’t for everyone but hold your hostel snobbery for this place. Located in the The Loop, this is the ideal location to meet like-minded travelers from around the world. You don’t have to bunk up, they do also offer private rooms with en-suites and rooms with shared bathrooms, so it’s not all communal living. The main benefit of this place is the free tours, pub crawls and continental breakfasts that are on offer. 

 

 

Written by Stuart Cooke, Blog Editor at MyBaggage.com an online luggage shipping company popular with visitors to the US from all over the world.