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Chicago city breaks: Your essential guide

Bursting at the seams with top restaurants, inspiring sights and shopping hotspots, Chicago really is one of the best cities in the US and the perfect destination for an autumn city break.

The Windy City has something for everyone, from sports stadiums and nightlife to museums and wildlife, but it can be hard to know where to start when the city has so much to offer. To help you out before your next trip to Chicago we thought we’d give you a rundown of the essential stop-offs in the Midwest’s biggest city. So pack your bags and get ready as we present your essential guide to Chicago.

Explore the Magnificent Mile
Michigan Avenue

Heading north from the Chicago River you’ll find Michigan Avenue - one mile of shops, restaurants and piers. Take a languid stroll down this glorious avenue and marvel at the beautiful architecture before heading into one of the many bars or restaurants to refuel.

Splash out at Alinea



If you’re a foodie and feeling a bit lavish you should definitely try out Alinea, one of only two restaurants in Chicago to hold three Michelin stars. Make a reservation before going and be sure to try out the chocolate desert which is constructed right in front of you on your tablecloth!

Take in the views on the Skydeck
Chicago view

Skydeck Chicago, on top of the Willis Tower, is a must for anybody who enjoys sensational views. The perfect spot for a landscape shot of the city - this observation deck is 1,353 feet above street level and is located on the 103rd floor!

Snap a selfie at Cloud Gate
Cloud Gate

Of course, no trip to Chicago is complete without taking a selfie with Cloud Gate, commonly known as “The Bean”. The sculpture was constructed by British artist Anish Kapoor in the mid 00’s and can be found in the centre of the AT&T Plaza in the city’s Millennium Park.

Brave the John Hancock Observatory
Hancock Observatory

Another observation deck well worth visiting is the John Hancock Skywalk, which is open until 11 pm daily. This open-air walk offers visitors access to phenomenal views any time of day and can be accessed using the fastest elevators in North America, which whiz you up to the 94th floor where the deck is found.

Be inspired at the Art Institute
Edward Hopper

One of the Windy City’s most popular museums is the Art Institute of Chicago. The institute recently added its Modern Wing to the building which homes contemporary artworks in a light, airy and beautiful setting.

Stroll down Navy PierNavy Pier  

Navy Pier is without a doubt one of the top things to do when in Chicago, even if it’s just to ride its 150 foot Ferris wheel. Stretching over 50 acres, the only problem with this pier is that there’s just not enough time in the day to see it all!

Grab a slice
Chicago Pizza

Deep pan pizza is a Chicago staple and a visit to the city isn’t complete until you’ve sampled a slice of the city’s finest. You’ll be spoilt for choice when it comes to where to dine in Chicago but for an authentic taste, head to Pizzeria Da Nella located on Fullerton Avenue.

Experience a little taste of luxury
Afternoon tea

When it comes to where you lay your head at night in the city there are a few hotels that are a cut above the rest. The 5 star Radisson Blu Aqua is located slap bang in the middle of the city and if you book now with us you can save 10 per cent on departures from now until the 20th October!

Chill out in Millennium Park
Millennium Park Autumn

Finally, there’s nothing quite like taking a walk in Chicago’s Millennium Park during autumn. The fall colours give a magical feel to the park and with 5 acres of garden to explore you really can lose yourself in this wonderful green space.  

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