Heads up: some of the links on this site are affiliate links. If you click and make a booking or purchase, I’ll make a commission (at no extra cost to you). I partner with companies I personally use and the $$ goes towards creating more awesome, free travel content.
Chicago has been a tourist hotspot for decades, but there’s always something new to see and experience, so even if you’ve visited in the past, this year’s a great time to book a trip to the Windy City.
Here’s just a small selection of reasons to check out Chicago right now and a smattering of tips that will make your stay totally seamless.
If you want to see works by great masters and modern geniuses, then The Art Institute of Chicago will wow you.
If natural history is more your thing, then the Field Museum has exhibits from all eras and is conveniently found adjacent to Shedd Aquarium, which is a wonderful place to catch marine life in motion.
Whether you’re traveling on a budget or going all-out, there’s an eatery or two in Chicago for you. Recent arrivals on the restaurant scene include French-inspired brasserie LeTour, North African-influenced spot Ragadan, and the home-grown heartiness of Second Generation.
There’s a lot to gawp at if you’re mainly visiting Chicago to do a bit of sightseeing. Whether gazing across the network of streets from the viewing deck of Willis Tower, taking in the old-school charm of Wrigley Field, strolling through Grant Park, or gathering with the crowds in the iconic Millennium Park, you’ll find something fresh and exciting around every corner.
Tips for traveling to Chicago
Even if you’re a seasoned traveler, it’s worth thinking carefully and planning ahead when visiting Chicago so that you can focus on enjoying what the city has to offer. Good moves for a smooth trip include:
Booking a private car to get you back to the airport in good time
Using a car service in Chicago to travel to and from the airport might sound like an extravagance, but it’s actually more affordable than you’d think and saves you from having to rely on hailing a cab or using an app to get a ride on the fly.
Reading reviews of accommodation options
Don’t just get wooed by a well-designed hotel website or a craftily written description of a rental apartment; actually, take the time to dig down into the reviews left by past guests to ensure that any accommodation that’s on your radar is actually up to scratch.
Checking the weather
Don’t just look at forecasts close to the time when your trip is scheduled, but also check into things like average temperatures and typical conditions for the time of year. That way you’ll know what you need to pack, as well as what types of activities will be a good fit for the weather.
Taking a paper map
While it’s perfectly possible to rely on your phone’s built-in navigation capabilities to get from A to B in Chicago or anywhere else, savvy travelers know that you can’t always trust digital devices. As such you’ll be thankful if you pick up a paper map of the city and keep it with you, so you’ve got something to refer to and use to get your bearings if your battery dies or your network coverage is patchy.
Planning for rest stops
Packing your daily itinerary with all sorts of activities in Chicago is fine to a certain extent, but you won’t have fun if you don’t also include time to rest and relax between sightseeing and traveling between spots.
If this has given you a taste of taking a trip to Chicago, it’s also worth mentioning that this is a city that will be a brilliant destination to visit year-round. Prepare properly, and you’re sure to have a blast.