Ever fancied following in the footsteps of Ferris Bueller and exploring the streets of Chicago? With its impressive architecture, rich culture and fantastic food spots, travellers can’t fail to be blown away by the Windy City.
From the legendary Loop where you can find historic sites like the Willis Tower and Grant Park to the musical landscape that includes the beloved Green Mill – Chicago offers something for everyone.
Where to stay in Chicago
If you are looking for a centrally located hotel, the Hilton Chicago is ideally situated in downtown’s Michigan Avenue. Once you have shopped until you have dropped, relax and take it easy on the seasonal sundeck where you can take in the glorious Chicago skyline.
For those that love luxury – The Peninsula ticks all the right boxes and is the premier choice for Hollywood stars and other VIPs. Their Grand Deluxe rooms feature magnificent views of Chicago's premier shopping district, Michigan Avenue, the historic Water Tower and more.
The Gwen hotel has a glorious past, steeped in history with a spectacular design making it totally instagrammable. It is situated just steps from Michigan Avenue and its plethora of shops
What to do in Chicago
Whether you have 24 hours in the city or longer, you won’t be short of things to do. Art lovers will make a beeline for the Art Institute of Chicago. This art museum is renowned the world over thanks to its incredible body of global works. Look out for temporary pop ups where you can find exhibitions as diverse as antique posters of the London Underground and Andy Warhol prints to collections showcasing the Bauhaus aesthetic.
The Skydeck in Chicago and the Willis Tower both afford magnificent views of the city – however you can expect to queue for up to a few hours at peak times for the Willis Tower, so it is wise to try and get there as early as you can.
From Navy Pier which is chock-full of rides and restaurants to Lincoln Park Zoo and the Planetarium – Chicago makes for an ideal family break! If you are looking for something to educate the children, head over to the Museum of Science and Industry which is one of the largest science museums in the world.
Where to eat in Chicago
Chicago is famed for its extensive and eclectic selection of eateries which caters for every budget and sensibility. Foodies will elate at the superb choice of Michelin-star restaurants which includes the three Michelin-starred Alinea. Here, you can expect exquisite tasting menus where every course is a theatrical masterpiece.
Fusing new American and Mediterranean cuisine, Good Fortune’s creative menu is one to try – expect tantalising dishes such as saffron bucatini and caramelised halloumi.
If you are looking for a traditional pizzeria, look no further than Gino’s East which is quintessentially Chicagoan thanks to its red-checkered tablecloths, Blues Brothers memorabilia nods to Chicago’s iconic landscape. Their signature secret-recipe dough has been delighting customers since 1968.
For a chilled-out Sunday brunch that attracts tourists and locals alike, Lula Café ticks all the right boxes and more. The dishes utilise local produce and change as often as on a daily basis.
Where to shop in Chicago
For the ultimate mall experience, Water Tower Place won’t disappoint – from Abercrombie & Fich to Victoria’s Secret and everything in-between, prepare not to leave this Chicago mainstay empty-handed.
You can’t say you have shopped in the Windy City without a trip to the iconic North Michigan Avenue which is also known by its affectionate moniker the ‘Magnificent Mile’. It is here that you can peruse the likes of Bloomingdales and Saks Fifth Avenue which sit alongside designer brands, boutiques and specialist shops. Get your credit cards ready!
Do you love all things vintage? Chicago has a myriad of vintage and thrift stores where you can find some truly exciting one-off pieces. Some of our favourites include: The Broadway Antique Market, Elliott Consignment and the Randolph Street Market which is a great little flea market that opens once a month in the West Loop.
Chicago like a local
One of the favourite things for a local to do is to take a drive down Lake Shore Drive, but for a real insider’s guide to driving in the city , head down the lesser-known but still incredibly scenic Emerald necklace where you can see some of the city’s most spectacular parks and squares via a lush 26-miles network of boulevards and streets. Don’t forget to crank up the tunes and play a Chicago-themed soundtrack.
If you are planning a trip to the city in the warmer months, you might want to take a trip to the beach. Our recommendation has to be Montrose Beach where you can find locals undertaking fun activities like kayaking and volleyball.
Chicago is known for its fantastic music scene and if you are hoping to catch a gig, you will truly be spoilt for choice. From the bijou ‘Hideout’ where you can see local bands play to the legendary Green Mill which is one of the city’s oldest bars – it is also home to one of the finest jazz clubs in North America.
Are you ready to discover Chicago? Get in touch with your Personal Travel Consultant today.