Grand American Adventures Official Blog

Our Latest Tales and Trails

Best Things to Do in Chicago in the Spring

Posted on 13-May-2015

They say that there’s no such thing as bad weather, just bad clothing. But even native Chicagoans complain this past winter was particularly cold. Damn that polar vortex!

Whether you think of it as the Windy City – actually that derives from politician’s hot air, not the climate – or America’s second city you’ll get a warm welcome from the Midwesterners who call Chicago home. For such a large place, the locals are remarkably “un-big-city’ish”. And who knows, you may even bump into Oprah?

Visit Chicago on our Historic Route 66 trip 



In my mind there are several things that make Chicago a stand out place to visit in the Spring, the architecture and the food being at the top of the list, with the added bonus you don’t need a car to get around – let the local rail network (“the L”) do that for you.

With days warming up, hop on a boat for an architecture tour on the Chicago River which gives you a fantastic perspective on the city’s sky scraping buildings that many argue are way better than Manhattan’s.

If you’d rather look down, not up, take the elevator to the 103rd floor of the Willis Tower, which locals still call by its previous name, the Sears Tower and see if you dare step out onto one of the protruding glass ledges 412 metres above the ground. A similar experience, Tilt 360 Chicago (which – can you see a pattern here? – natives also call by its previous name, the John Hancock Observatory) – opens this spring and levers thrill seekers out some 1,000ft over the city’s streets.





 Enough up and down. Time to eat. Chicago is home to deep-dish pizza and while the locals may scoff a bit – in the same way Brits roll their eyes when the rest of the world thinks we just live off fish and chips – it has to be said, the local version is flipping tasty. Try one at Lou Malnati’s or Pizzeria Uno: both still argue who invented this style of pizza, which has a crust up to 3 inches tall and a molten lake of sweet, tangy tomato sauce. You can positively hear your arteries screaming, but what a way to go.




If you set your culinary sights a bit higher, Chicago has 25 Michelin-starred restaurants including Alinea, which was recently named number 9 in the World’s Top 50 Restaurants. If you want a reservation you buy a ticket, which can run up to $265 excluding service, tax or drinks, availability of which is advertised on their Facebook page 2-3 months in advance.

Luckily, there are plenty of other fantastic eateries in town where you won’t have to sell your granny in order to be able to dine there. One of my favourite places for brunch is Mindy’s Hot Chocolate - start with the warm doughnuts, move onto the brioche French toast and then maybe share some Ham & Grits or Mac & Cheese.

And then you can bundle up and go for a run along Lake Michigan to work off a few calories and imagine the beaches here heaving with families and people playing volleyball come summertime. Hey, was that Oprah who just jogged past?!

And of course, the shore of Lake Michigan is the start of the famous Route 66 and Grand American Adventures offer a 14 day road trip down this famous road, visiting famous spots like the Grand Canyon and the desert city of Las Vegas.


Visit Chicago on our Historic Route 66 trip 


Will Hide is a London-based travel writer who spent 12 years on the travel desk of the Times before turning freelance. He still writes regularly for the Times as well as the FT, Telegraph and numerous magazines. You can follow his travels at Been There, Done It.


Topics: USA, General, USA East