Ah, Chicago! This city of blues and deep-dish delights is a feast for the eyes, ears, and appetites. Whether you’re coming to The Windy City for business, pleasure or a romantic getaway, there is always something to sink your teeth in. The restaurants are quite diverse, and even the local entertainment is worth the visit. Go to all of the typical tourist hot-spots, sure, but also make time to check out some of the popular venues, eateries, and attractions that will have you coming back again and again. We’ve rounded up the best of the best in this Chicago City Guide plus the best hotel deals for your stay.

The Must-Sees and Must-Dos

While there are plenty of attractions that will be top on your list, you may want to make time for checking out some of the astounding architecture in the city. Holy Name Cathedral is one of these sprawling buildings that has vaulted ceilings and impressive stonework for visitors to enjoy. The cathedral is on North State Street and is accessible by Chicago’s Red Line bus route or by car via North Lake Shore Drive. Those interested in getting a bird’s eye view of the Chicago skyline will absolutely adore the opportunity to visit The SkyDeck at Willis Tower. At 1353 ft., visitors have the chance to take some of the most breathtaking photos thanks to panoramic views of the skyscrapers, and there are glass ledges for guests to stand on if they’re feeling brave enough to do so. They even rent out the 99th floor for special events with a glittery view of the night sky in the Windy City.


Recommended in the Chicago City Guide is the Sears Tower also  known as the Willis Tower skydeck glass ledge in Chicago

Photo Credit: Charlotte


There are plenty of spots in Chicago to have a seat on a bench and watch the world go by, but if you’re in the mood for some casual meandering, The Chicago Riverwalk is the best place to do it. The promenade winds its way along the most prominent stretch of the Chicago River, past several key neighborhoods, restaurants, and shops. This is also the infamous portion of the river that’s dyed green during St. Patrick’s Day festivities, so you’re bound to find a pub or two along the way. This is the place to be for taking a romantic stroll or excellent Instagram photographs.


A must do in the Chicago city guide is a stroll along the Chicago river


Can’t Miss Events

Chicago is one of those towns that has an amazing lineup of summer festivities so if you are planning a weekend getaway to this city, be sure to check Thrillist’s calendar of events. Blues fans won’t want to miss the free Chicago Blues Festival in June while beer connoisseurs will want to hit the Chicago Ale Fest, also in June. Foodies should hit the city in early July for the Taste of Chicago or just about any other summer weekend for some type of food fiesta. Of course, the star event for most people is Lollapalooza but if you don’t have tickets there are plenty of other events to check out.

Outdoor Activities and Sports

If you’re in town during winter, there are tons of chances to warm up indoors. One of the most exciting attractions to visit during the colder months is the United Center, where NHL teams battle the Chicago Blackhawks. The crowds are electric and there are always tons of great things to drink and eat while watching the game. Once hockey season is over, the Chicago White Sox hit the batting cages and US Cellular Field as Major League Baseball kicks into gear. Go to the ballpark for an All-American frank and a pint of ice cold beer while watching world-class athletes make their way to the World Series.


c sportys


During the summer months, the shores of Lake Michigan are dotted with beach goers, and North Avenue Beach is one of the best for taking a dip or sunbathing for the day. The beach is located on North Lake Shore Drive and has a lifeguard on duty during normal operating hours for swimmer safety. The North Avenue Beach House is made in the shape of a cruise liner and features concessions and changing rooms for convenience. Lake Michigan also provides a stunning backdrop for the city to glint against, and there are always excursions out on the water for appreciating the beauty of the city from afar. Tall ships hit the harbor at the beginning of May and the Tall Ship Windy is one of those that offers boat rides out on Lake Michigan. Chock-full of history and vintage flair, passengers will be able to experience windswept sunsets before heading back in.


North Avenue Beach House


Eating on a Budget

You can’t go to Chicago without having a deep-dish pizza, and just because you’re in the big city doesn’t mean you have to spend a fortune to get the real thing. Lou Malnati’s Pizzeria is absolutely perfect for satisfying a huge appetite while on a tight budget. The most fortunate thing about ordering from Lou’s is the sheer volume of stores within Chicago, so no matter where you find yourself, there’s a place to sit in and eat, or order take-out or delivery. They ship their pizzas nationwide too, so if you’re craving one when you get home, visit their website to order a slice of Chicago.


Now that's a deep dish pizza! Photo Credit: Krista

Now that’s a deep dish pizza! Photo Credit: David Wilson


Delis aren’t just a New York City thing, there are also diners and delis in Chicago that make to-die-for Reubens and Monte Cristos. The Eleven City Diner is in both the North Side and South Loop neighborhoods and has all of the classic meals and sandwiches you could ever think of ordering. This is also a great place to stop in at for a diner-style breakfast that won’t break the bank.


Photo Credit: David Wilson

Photo Credit: David Wilson


Light and healthy meals aren’t completely obsolete in Chi-town, so if you’re looking for something easy on your wallet and healthier than anything your hotel can serve up, go to Niu Sushi on East Illinois Street. They have more than sushi too. You can fill up on seafood-free food like chicken teriyaki or go for vegetarian fare. The mantra never rang truer: When all else fails, go for sushi! Better yet, go for sushi, and make it a night of bowling (there’s a bowling alley next door).


Fine Dining

If you’re looking for an upscale place to dine out at while in the city, you won’t find it difficult to locate a good spot. Joe’s Seafood, Prime Steak, and Stone Crab is a top-notch restaurant perfect for romantic nights out or important business meetings. Their seafood is the most mouthwatering you can find in the whole of Chicago, and although the price is higher than that of an average meal, you’ll be pleased to see hefty portions land at your table. If star quality is something you crave, Chicago is full of venues to enjoy a few celeb sightings, and fans of the FOX reality show Masterchef can seize the opportunity to dine at Judge Graham Elliot’s bistro, appropriately named The Graham Elliot Bistro. You’ll be met with gourmet fare that’s rich in new-school pizzazz, and the wine list is the cherry on top of a perfect evening.


Chicago city guide recommends eating at Joes


Nightlife in the Windy City

Some folks aren’t so keen on hitting up nightclubs or noisy bars. For the sophisticated individual who just wants to have a few appetizers and an icy mug of craft beer after seeing a show or going to a game, the Girl & The Goat is your ticket to a low-key night with friends or your partner. They serve an exquisite selection of wines by the glass or bottle, and their oysters are a superb late night snack for two. Just go down to the Randolph Restaurant Corridor on West Randolph Street, and look for the restaurant with the goat sign. You can’t miss it!


Wood Fired Oysters from the Girl & The Goat

Wood Fired Oysters from the Girl & The Goat


There are widespread entertainment options in Chicago. There are dozens of jazz clubs, theaters, and auditoriums that feature talented acts. Two of the places where you can see local and international artists are The House of Blues & Second City. The House of Blues in Chicago is situated right on the river at North Dearborn Street. The unique shape will give it away, but what’s going on inside is much more thrilling. Guests can see acts in all of the major genres of music most nights of the week, and you can purchase tickets for the show you’d like to see in advance. Second City is a world-renowned comedy club that puts on skits, improv, comedy games, and stand-up acts year round. You can find unlimited laughs on North Wells Street at one of a couple different performance areas that serve food and both alcoholic and non-alcoholic beverages.


Hidden Gems

Chicago is the home of a heavy load of American history, and there are lots of hidden gems in town where you can escape the throng of tourists while having a drink and meal in a club that celebrates the Prohibition Era’s speakeasies. The Violet Hour is a community secret on North Damen Avenue off the northern tip of Wicker Park that offers a unique aspect of nightlife with dimmed lights, small snacks to nibble on, and a comprehensive menu of cocktails for your savoring. There are some house rules like dress code and a zero-tolerance policy on cell phone use, but the experience is well worth it!


The Violet Hour

The Violet Hour


Another interesting spot to stop in at is The Magic Parlour, which is situated at the Palmer Hilton House Hotel on East Monroe Street in the downtown core. It seems simple enough, but this completely out-of-the-box evening of illusions, magic tricks, and mind reading is the perfect way to spend an evening out. You will be able to witness tricks that seem to bend reality while enjoying complimentary libations. The night will be utterly magical.

Let us know if you have more insider info that we should add to our Chicago City Guide!

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