Chicago is affectionately nicknamed ‘The Windy City’, though it’s not actually America’s windiest city. It’s also famously known as the starting point of the historic Route 66.

Check in to your hotel and get settled after your flight, then ease into your Chicago city break with a leisurely walk around the city. An early evening stroll along Chicago’s Riverwalk is a lovely, low-key way to get your bearings after a long-haul journey.

Embrace the culture straight away and try a deep-dish pizza for dinner, a Chicago classic. Lou Malnati’s and Giordano’s are popular spots to try.

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After settling in and getting your bearings yesterday, it’s time to dive into Chicago’s best-known sights. Your Chicago CityPASS® is included for the duration of your stay, giving you access to some of the city’s best must-see destinations.

Start your exploration of the city with a visit to The Skydeck in the iconic Willis Tower. Feel the rush of standing on a glass ledge suspended 103 floors over the city. All-glass balconies offer uninterrupted views of the city and the perfect opportunity to capture some incredible photos. Are you brave enough to step out onto the ledge?

For lunch, you’re spoilt for choice: there’s a food hall inside the Willis Tower itself, or head into The Loop nearby for a wider range of food halls and reasonably priced options.

In the afternoon, head for a relaxed visit to the Art Institute of Chicago, where you can skip the queue with the Fast Pass included in your Chicago CityPASS® ticket. Allow a few hours to explore, with highlights including the Impressionist galleries and Grant Wood’s iconic American Gothic. There’s a lovely café inside the gallery, perfect for a sit-down and a chance to rest your feet.

Once you’ve soaked up the art, it’s just a short stroll to Millennium Park, home to the unmissable Cloud Gate, better known to locals as ‘The Bean’. Watch the city skyline warp and shimmer across its seamless, polished steel surface, especially magical at sunset.

Top tip: Book your Skydeck Chicago tickets in advance and arrive early, as queues build up quickly at this popular attraction.

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Prepare yourself for a jam-packed day of sightseeing with your Chicago CityPASS®. Start your day with an Architecture River Tour, where you’ll cruise along the Chicago River for a unique view of this stunning city from the vantage point of the water. Enjoy a coffee near the river before making your way to Museum Campus, located on the shore of Lake Michigan just south of downtown Chicago.

Once you’ve arrived, your next stop is the Field Museum, one of the world’s largest and most famous natural history museums. Your ticket includes general admission to the permanent halls and galleries, plus a choice of two select ticketed exhibitions and/or 3D movies (some exhibitions and experiences are not included).

After time exploring ancient artefacts in the Field Museum, head to Shedd Aquarium, located right next door. See penguins fly through chilly waters, spot sleek sharks cruising overhead, and count the suckers on an octopus’s arms. Enjoy touch exhibits, animal talks and a 4-D Experience, all included in your ticket.

If you’ve the energy after a busy day, Museum Campus has lovely lakefront views for a relaxed end to the day before heading back to your hotel.

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Enjoy a relaxed morning before your trip comes to an end. Take a final walk on Magnificent Mile (Michigan Avenue) to take one last look at the city or do some casual shopping before your departure. Keep an eye out for the “Begin Route 66” sign at Adams Street, marking the spot where the historic route officially begins. First travelled in 1926, it has also been symbolically extended to the lakefront at Navy Pier for its centennial, creating a pier-to-pier connection all the way to California.

Alternatively, take another trip to Millennium Park to see ‘The Bean’ in the daytime and the Crown Fountain, a famous interactive art sculpture. It features two 50-foot glass block towers with LED screens displaying the faces of local residents, who periodically pucker up and spit water into the splash zone below.

However you choose to spend your final hours, we hope Chicago has left you with plenty of happy memories to take home.