On a cross-country Amtrak adventure in the USA, Richard Holmes stops over to sample the highlights of Chicago and Denver.

There was never going to be enough time to properly explore Chicago, with just less than 24 hours for a taste of the ‘Windy City’.

Travel to Chicago and Denver: Riding the rails

I was on a cross-country adventure, travelling from New York to San Francisco by Amtrak train, and I couldn’t pass through the Midwest without a stop in the city made famous by everyone from Al Capone, to Oprah Winfrey, to Barack Obama.

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After dropping my bags at the newly renovated Omni Chicago Hotel set right on the city’s so-called Magnificent Mile, I wandered south to where it all began. Here, where Michigan Avenue crosses the Chicago River, the impressive DuSable Bridge pays tribute to the Frenchman who first settled in the city in the late 1700s. But Jean Baptiste Point du Sable would barely recognise the place these days. Through boom, bust and raging fires, Chicago has cemented its position as the commercial heart of the Midwest, its prosperity written in the skyscrapers that etch the city’s impressive skyline.

Travel to Chicago and Denver: Riding the rails

While open-top buses and walking tours reveal local highlights, the Chicago Architecture Foundation River Cruise aboard First Lady Cruises is the best way to get a sense of the city. These hour-long trips take in the canals of the river flowing through the city, as entertaining guides unravel the history and architecture of Chicago.

Travel to Chicago and Denver: Riding the rails

The next morning, I dashed across town to take in the views from the top of the Willis Tower, the spectacular 99th-floor Skydeck offering vistas across the city and Lake Michigan, the second largest of America’s Great Lakes.

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On the lakeshore below my feet, Millennium Park is home to the remarkable Art Institute of Chicago, the glorious Jay Pritzker Pavilion, and the quirky polished steel sculpture dubbed Cloud Gate, but affectionately referred to as, simply, The Bean.

Travel to Chicago and Denver: Riding the rails

On the stroke of 2pm, the double-decker California Zephyr edged slowly out through the suburbs of Chicago to Denver, Colorado.Morning brought distant views of the snow-capped Rocky Mountains and the skyline of Denver through the mist.

Dubbed the Mile High City, Denver revels in its laid-back approach to life. Although a major commercial and transport hub, from the atmosphere on the streets it’s easy to think the entire city spends its days hiking, biking and sipping beer.

Travel to Chicago and Denver: Riding the rails

That vibrant social culture was apparent the moment I stepped off the train into the 120-year-old Union Station. Revamped in 2014, the ticket hall has become a vibrant communal space for locals – ‘Denver’s living room’, they call it – who flock here to enjoy the craft beers on tap at Terminal Bar, the luscious ice cream from Milkbox Ice Creamery, and the daily charcuterie and sandwiches on offer at Acme Delicatessen.

Part of the station’s rejuvenation is the inclusion of a stylish boutique hotel, The Crawford. With luxury rooms scattered across the station building, many with views of the platforms, it was the ideal overnight break for my cross-country rail journey.

Travel to Chicago and Denver: Riding the rails

And when it came to sightseeing, there was an obvious first stop: the Colorado Railway Museum. This charming open-air museum is home to more than 100 carriages and locomotives dating from the early days of steam through the heyday of the American railroad.

Travel to Chicago and Denver: Riding the rails

While many shops in Denver’s pedestrianised 16th-Street Mile are famous international brands, seek out the I Heart Denver store inside the Denver Pavilions centre. More than 135 local artists and designers showcase their work here, giving an enormous boost to the local creative economy.

Further down 16th – take the free shuttle bus if you tire – you’ll find the Golden Triangle Museum District. Choose between the History Colorado Center, the Molly Brown House, remembering the famed Titanic survivor, and the Clyfford Still gallery. If you have time for just one, make it the Denver Art Museum, an eye-catching fusion of art and architecture.

Travel to Chicago and Denver: Riding the rails


VALUE FOR MONEY The Chicago CityPASS and Denver Passport are great for saving a few dollars on visiting major sights.

MUST-SEE SIGHT It might be cheesy, but that’s no reason not to take a selfie at the official Mile High step on the side of Denver’s State Capitol building.

WHERE TO EAT Don’t leave Chicago without a taste of the city’s famed deep-dish pizza. Locals swear by Pizzeria Uno and Lou Malnati’s.

NICE TO KNOW Plan ahead to take in a concert at the iconic Red Rocks Amphitheatre, a 30-minute drive from Denver.

Travel to Chicago and Denver: Riding the rails


WHEN TO GO Avoid the summer holidays when demand and prices tend to spike. Aim for the ‘shoulder’ seasons of April-May and September-October. For winter travels, Denver is close to a number of leading ski resorts.

GETTING THERE British Airways flies daily from South Africa to London

Heathrow, with connections to both Chicago and Denver (and 23 other US destinations). ba.com

VISAS South African passport-holders require a visa to visit the United States. Begin your application at https://za.usembassy.gov/visas

FIND OUT MORE Go to ChooseChicago.com and visitdenver.com to start planning. Book Amtrak tickets online at amtrak.com