My Chicago City Guide might tempt you to explore somewhere new in America. I’ve visited many times over the years because Homeboy’s family live there. From the lovely lakefront to the spectacular skyline, amazing architecture, splendid shopping and fabulous food, you’ll find plenty to keep you occupied. Read on for my Chicago City Guide to discover the top tourist attractions in Chicago and interesting neighbourhoods like Andersonville, Wicker Park, Roscoe Village and Logan Square.

chicago city guide, the bean

The Bean

Chicago City Guide to the Top Tourist Attractions

Lovely Lakefront: Chicago is very scenic thanks to Lake Michigan which has an amazing shoreline which stretches for miles along Lake Shore Drive. As soon as the sun shines you’ll see locals cycling, rollerblading, skateboarding, walking and jogging beside the expansive lake. Make sure you take a stroll along the lakefront on your visit where you’ll discover beaches, cafes and marinas. The kids might enjoy Navy Pier which has a Children’s Museum, Centennial Ferris Wheel, IMAX Theatre and restaurants.

chicago city guide, marina, navy pier centennial wheel

Lakefront Marina and Navy Pier Centennial Wheel

Spectacular Skyline: After the great fire in 1871 much of the city had to be rebuilt which has resulted in a spectacular downtown skyline. Make sure you take a moment to enjoy that skyline when you drive into the city during the day and at night because it really is beautiful. There’s an interesting mix of architecture in the city which includes plenty of skyscrapers. You can enjoy the best view of the city from the Willis Tower Skydeck on the 103rd floor where you can walk out onto a glass ledge and look down if you dare (formerly the Sears Tower).

chicago city guide, willis tower skyscraper

Willis Tower Skyscraper

Amazing Architecture: If you’re a fan of architecture then you really should book yourself a seat on the First Lady River Cruise by the Chicago Architecture Foundation. You’ll discover the importance of the river to the city and see the buildings close up. The architecture is diverse ranging from the European Renaissance Wrigley Building built in 1924 to the Merchandise Mart art deco warehouse from 1930 to the curved green tinted façade of 333 West Wacker Drive built in 1983. With modern buildings like the Trump International Hotel and Tower plus the Aqua with its wave-like balconies, there is something for everyone. You can also see for yourself how Chicago is revitalizing the river banks and creating outdoor parks, seating areas and much more. Fans of Frank Lloyd Wright can tour his home and studio located in Oak Park through tours by the Frank Lloyd Wright Trust plus a number of his famous Chicago buildings.

chicago city guide, riverboat tour

Architecture River Cruise

Astounding Art: Some of the best art is located outside which you can view for free. Head for Millennium Park where you can see your reflection in The Cloud Gate, otherwise known as The Bean by Anish Kapoor. Close by is the Crown Fountain by Jaume Plensa, a Spanish artist. This is comprised of two fifty-foot glass block towers with projected images of Chicago citizens.

chicago city guide, crown fountain

Crown Fountain

While you are in Millennium Park you can also check out the Jay Pritzker Pavilion. You can also see Agora by Polish artist Magdalena Abakanowicz at the south end of Grant Park. This is a group of 106 iron sculptures without arms or heads. A monumental sculpture by Pablo Picasso can be found in the Daley Plaza in the Chicago Loop which was the first piece of public art in the vicinity and is now a famous landmark. Flamingo is also very impressive sculpture by Alexander Calder which has been located in the Federal Plaza since 1973. If it’s cold and rainy outside you can visit the Art Institute of Chicago which houses a collection of around 300,000 works of arts which range from ancient times to modern day.  If you prefer contemporary art head for the Museum of Contemporary Art.

chicago city guide, flamingo sculpture

Flamingo Sculpture

Awesome Attractions: Those interested in museums will certainly be kept busy with a trip to the Field Museum which you’ll find in the Museum Campus. You’ll find dinosaurs to Egyptian mummies and so much more. While you are in the area also check out the Adler Planetarium and the Shedd Aquarium. You can also visit Lincoln Park Zoo and the wonderful Chicago Botanic Garden.

chicago city guide, crime tours

Chicago Crime Tours

Tempting Tours: If you’d rather let a tour guide show you around hop on the Big Bus Tours Chicago and you’ll get to explore the downtown area and shown the city landmarks. The Chicago Crime Tours will give you the history of the mobsters and gangsters which is fun. As I’ve already mentioned, the Frank Lloyd Wright Tour is a must for any architecture fans as is the river boat tour.

Chicago City Guide to Entertainment, Restaurants and Shopping

Exciting Entertainment: You can book to see Broadway Shows in Chicago and many alternative plays and productions. Music venues are plentiful ranging from rock, blues, jazz and every genre. Other entertainment includes bowling, going to the movies which is much cheaper than the UK, comedy clubs, festivals and plenty of free events throughout the summer. Sports fans might like to watch a baseball game at Wrigley Field, the home of the Chicago Cubs or visit Soldier Field, the home of the Chicago Bears. Check out The Reader for information about current events.

chicago city guide, theatre

Chicago Theatre

Fabulous Food: You certainly won’t go hungry in Chicago that’s for sure. The city is famous for deep pan pizza, BBQ ribs and steak so perhaps try these dishes while you are in town. There are plenty of healthy restaurants as well like Lyfe Kitchen which serves up vegan, vegetarian and nutrient packed dishes. For breakfast try Yolk for eggs or Kanela Breakfast Club which is a Greek and American fusion. Wholefoods, the premium supermarket can be found throughout the city which often have seating areas so you can buy take-out food which you can eat in. If you want to step back in time try Margie’s Candies which is an old fashioned ice cream parlour dating back to 1921 where you can enjoy sundaes, splits, shakes and take home some famous candies. I spotted quite a few food trucks downtown so you can also track those down.

chicago city guide, yolk restaurant

Yolk Restaurant

Splendid Shopping: If you’re planning a shopping trip then The Magnificent Mile on Michigan Avenue is a must. Here you’ll find all fashion stores ranging from designer high end luxury through to Top Shop. Department stores including Bloomingdales, Marshalls, Nordstrom, Neiman Marcus and Saks Fifth Avenue. More high end designer stores can be found in the Gold Coast vicinity which is North of downtown on the Lake Michigan Shoreline. From Barneys New York to Prada and Marc Jacobs, it’s a fashionistas dream. For independent fashion stores try the neighbourhoods like Logan Square, Wicker Park and Roscoe Village.

chicago city guide, the magnificent mile

The Magnificent Mile

Chicago City Guide to Interesting Neighbourhoods

Aside from the downtown area, Chicago has some interesting neighbourhoods to explore. I’ve written about four of my favourite areas but you can find more information at the Choose Chicago Website. Logan Square: My sister in law lives close to Logan Square (Northwest side of city of Chicago) and over the years it has developed into Chicago’s hipster vicinity. Even an Uber cab driver referenced that it was now hipsterville! Here you’ll find some great eateries one of which is Lula Café serving buttermilk pancakes, breakfast burritos, tasty egg dishes, grits and buckwheat gnudi. With new coffee shops and bars springing up it’s a great place to hang out for an afternoon. You’ll also find a smattering of independent shops like Wolfbait and B-Girls selling jewellery and fashion pieces made by local artisans.

chicago city guide, logan square

Logan Square

Wicker Park: Before Logan Square became cool, Wicker Park (and Bucktown) held the hipster crown. It’s still an exciting part of the city to explore which you’ll find within the West Town community area of Chicago west of the Kennedy Expressway. There are some great food options like the Umami Burger joint we tried serving up Truffle burgers, Big Star bar with Mexican bites to go with your beer and The Wormhole Coffee where everyone has an Apple Macbook. This is a great place for fashion browsing from Urban Outfitters to Free People, G Star Raw, Brooklyn Industries and more. The vintage stores, thrift outlets and independent boutiques will satisfy your retail cravings.

Andersonville: Located on the North Side of Chicago, Andersonville has a Swedish heritage a growing lesbian and gay community. With a mix of independent fashion stores and vintage furniture shops, it’s a brilliant place to browse. I always pop into the big shoe shop called Alamo which has a vast stock of footwear. In terms of eateries, you have an extensive choice so you won’t go hungry. I’ve eaten at Jin Ju, the Korean bar restaurant several times which has always been great.

chicago city guide, andersonville


Roscoe Village: For a more laid back area to explore saunter down to Roscoe Village which is located on the North Side of Chicago between the North Centre and Lakeview. With tree lined streets, it has a relaxed vibe so you can enjoy dining alfresco when the sun is shining. I love to eat at Victory’s Banner which is a vegetarian and vegan restaurant where all the staff are students of meditation studying with the Indian Spiritual Master Sri Chinmoy. The food is amazing, the interiors are super cute and the staff are friendly and serene. There are numerous boutiques dotted along the road so you’ll enjoy an afternoon there.

Chicago City Guide to Hotels and Travelling

Hotels range from top end establishments like the Millennium Knickerbocker to the Waldorf Astoria and the Drake Hotel. For boutique hotels try The James, The Silversmith and if you want modern check into the W. We booked an apartment overlooking Navy Pier via Airbnb with spectacular views which was incredible. The airports are O’Hare and Midway. Travelling around the city is easy thanks to plenty of mini cabs you can flag down on the street. We also used Uber taxis while we were there. There is so much more to do in this city, this is just a snap shot, so I’m sure you’ll enjoy your visit. Just remember that it gets very cold in the winter and in the summer it is quite hot!

Author: Homegirl London. Photographs: Homegirl London. Thanks: Homeboy and mum for travelling with me and Homeboy’s family for driving us around.


Chicago City Guide by Homegirl London