If you’re about to do a spot of Chicago sightseeing, then these are eight things that shouldn’t be missed. Click here to reveal more information!

Chicago Mayor, Rahm Emanuel, set an ambitious goal of attracting 55 million visitors per year to the Windy City by 2020. Last year saw more than that number of tourists enjoy a trip to Chicago. But what brings all those visitors to the city? We’ve researched some of the best Chicago sightseeing opportunities. Whether it’s the arts, the great outdoors or learning about the city’s history there is something for everyone.

Our Guide to Chicago Sightseeing

Founded in 1830, Chicago has a rich history. It became the largest city in the midwest as a transport hub, linking water and rail. If you want to dip into Chicago’s past, add these to your list.


The Chicago History Museum

The Chicago History Museum - AssistAntFormerly the archive for the Chicago Historical Society, this museum is the place to go to learn about the past of the Windy City. The museum has a full program of events, so it’s definitely worth checking the calendar before your visit to see what’s on. The Museum is open every day of the week and has a Cafe so there’s no need to cut your visit short if you need something to eat. As one of the preeminent Chicago points of interest, the museum is home to several collections. You’ll find the museum at 1601 North Clark Street, in Lincoln Park. The Colonial Style building is hard to miss, and it has been expanded several times to house the impressive collection.

Historic Pullman Foundation Visitor Center

The railway has played a huge part in Chicago’s history. One of the biggest names in railway is George Pullman, the man who founded a town to house the employees of his carriage building company. A must do in Chicago for railway fans is the Historic Pullman Foundation Visitor Center. The center is the starting point of a walking tour which takes in the points of interest of the district. The center itself describes the preservation efforts for the area and displays furniture and other items from Pullman’s life.

The Arts

From the opera to grassroots comedy, there is a wide variety of arts-based tourist attractions in Chicago. Here are two of the top venues to spend your evenings.

The Second City

This theatre has seen some of America’s primo comic talent walk its boards. Tina Fey, Bill Murray, and Stephen Colbert have all honed their routines at Second City. A visit today will let you see both sketch and stand-up comedy from some of America’s rising stars. And if you think you’re funny, they run classes and workshops for the up and comers. The Chicago venue for Second City was the first, opening its doors in the 1950’s. It’s been giving comics a chance, and audiences a laugh for over half a century. You can also find Second City in Toronto and Hollywood.

Museum of Contemporary Art

A Chicago must see, the Museum of Contemporary Art is home to one of the largest collections in the US. As well as displaying its own collection, the museum hosts regular exhibitions and touring shows. The busiest day for visitors to the museum is Tuesday when it offers free entry. So if you’d like a chance to enjoy the collection in relative peace, then Wednesday or Thursday are your best days to visit.

Out and About

Chicago also has plenty to offer in terms of recreational spaces. It is home to several parks and interesting walks. Here are a few of our favorites.

Chicago Riverwalk

Enjoy an evenings stroll alongside the river, which has many bars and restaurants that adorn its banks. Walking this path allows you to see parts of the city that aren’t otherwise visible. The river also provides a way to get around. You could walk to a bar, but then take one of the water taxi’s to make your dinner reservation on time.

Lincoln Park Zoo

Founded in 1868, Lincoln Park Zoo is one of the oldest in North America. Open every day of the year, and with free admission, there are no barriers to enjoying all that the zoo has to offer. From Aardvarks to Zebras, Linkin Park Zoo allows the visitor to see animals from all around the world. The zoo has a breeding program and often has newborn animals to coo over.

Destination Meals

Chicago has a multicultural demographic, and that’s reflected in the eateries that are available to visitors. If you’d like something a bit different while you’re visiting, try one of these locations.

Carnitas Uruapan

This is a lunch destination as it closes at 5 pm, but if you want the very best pulled-pork tortillas then this is the place for you. The restaurant was founded in 1975 with the aim of providing authentic Uruapan-style cooking. The restaurant is in the heart of the Mexican community, and while you’re visiting you can enjoy some of the art in the area which includes murals. You might be in Chicago, but that’s no reason you shouldn’t get a taste of Mexico!

Balmoral Brewery

Balmoral Brewery Chicago - AssistAntIf you want to find out how one of Chicago’s favorite beermakers plies their trade, then visit the Balmoral Brewery on Sunday morning. You’ll get a full tour of the facility, and the chance to try some of the beer. As a souvenir, you can take away a pint glass. The brewery also has a shop where you can buy all their regular beers. It also offers exclusive ‘adventure cans’ only available through the shop. There’s no regular schedule and they’re limited in supply, but you might be lucky enough to visit on a day when something special is on offer.

So Much to See

These are just a few of the many Chicago sightseeing attractions you can enjoy. If you’re planning a visit, we’d love to help make it as pleasurable as possible. Our VIP service is the perfect way to get from O’Hare to your hotel. Or why not make your trip one to remember by hiring a chauffeur-driven limousine to drive you from place to place. We have more than 10-years of experience in concierge service, supporting you to make your visit to Chicago something you will remember forever.

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