- Chicago is a Midwest gem with a vibrant art, culture, and sports scene.
- There are many hotel, restaurant, and activity options when planning a trip to the Windy City.
- Visit Insider’s hub for travel guides, tips, and recommendations.
From the food to the sports teams, the extremely vibrant arts and culture scene to the politics, it’s virtually impossible to capture Chicago in a short stay. No matter what you’re interested in, the Windy City offers experiences to pique your interest if you’re willing to go out and explore.
Parking a car might be more trouble than it’s worth, so grab one of the city’s handy rental bikes or scooters, take public transit, or use a ride-hailing or taxi service to make the most of your time. Better still, build a little time to walk around the neighborhoods wherever you happen to be if you want to feel the city’s essence and energy in your bones.
Walking and looking around the city is one of the best ways to find new and interesting things to explore. Chicago is an eminently walkable city, and you never know when you’ll find a new piece of art or architecture, or even someone’s beautiful front garden that seems like it was put there just to brighten your day.
If you’re a creative person, it’s difficult not to be inspired by Chicago’s energy. Be prepared to reach early and often for your pen, sketch pad, camera, laptop, or other tools of the trade. And build some breathing time into your busy vacation schedule so you can go a little deeper into whatever your heart desires as you find it. If you’re the kind of person who loves to keep headphones on at all times, take them off once in a while and listen to the sounds of the city.
You can fly into the Second City through Chicago O’Hare International Airport or Chicago Midway International Airport. O’Hare is a quick CTA Blue Line trip away from most of what you’re itching to experience, while the Orange Line can take you to or from Midway. The CTA is Chicago’s public transit system, operating the trains and buses within the city. If you venture into the suburbs, you can use Metra trains or Pace buses, from separate companies that sometimes cooperate.
To use CTA trains and buses, you’ll need to purchase a Ventra transit card and put money on it — Ventra iOS and Android apps can help you load your card.
Chicago Union Station is a major rail hub with not only Metra commuter trains traveling to and from the suburbs but Amtrak trains welcoming visitors to the city. If the romance of cross-country train travel appeals to you, Union Station is conveniently located within walking distance of many popular destinations.
Since Union Station is in the heart of downtown, you’ll have plenty of local transit options at your disposal. And if you’re a pop-culture fan, you can see many of the city’s filming locations while you’re taking in the sights.
The Blackstone Hotel is a unique piece of Chicago history. It was built between 1908 and 1910 and is on the National Register of Historic Places. After falling into disrepair, it was fully restored in the early 2000s and reopened to the public in 2008. The Blackstone was envisioned as a luxury hotel and gained a reputation as the “Hotel of Presidents,” since many American presidents have stayed there over the decades. Today, the hotel offers plenty of modern amenities with historic flair (and it’s pet-friendly).
The Publishing House Bed and Breakfast also boasts a rich history — the building it occupies was built as the Free Methodist Publishing House in 1909. The arty charms in each of its 11 rooms offer a boutique, highly personalized experience. If you love to feel the personality of the place where you’re staying, look no further than the Publishing House.
The Villa Toscana Bed and Breakfast takes you farther north, up to the vibrant Boystown neighborhood, also known as Northalsted. The Victorian guesthouse, built in 1892, offers easy access to a wide array of nightlife options if you want to see Chicago shine. While service dogs are welcome, other animals, including emotional-support animals, are not. Additionally, guests under 18 are not allowed to stay in this establishment.
Whether you’re vegetarian, vegan, or just out to enjoy delicious food, you need to visit Soul Veg City. Once known as the Original Soul Vegetarian, Soul Veg City is Chicago’s longest-operating vegan restaurant — it recently celebrated its 40th birthday. You can’t go wrong with Soul Veg’s kale greens and cornbread muffins, and the spicy chicken sandwich will satisfy all your spicy chicken cravings.
Irazu is a Costa Rican staple that’s been serving delicious food and warmth since 1990. While the restaurant has flourished, the concept is still a small family business at heart. The menu offers traditional options for single diners as well as family meals and catering. During the pandemic, Irazu began offering bring-your-own-spirit kits for a tropical cocktail experience outside the restaurant. Whatever you do, try the oatmeal shake. You won’t regret it.
Do you have an insatiable sweet tooth? Let us introduce you to Jennivee’s Bakery. While custom cakes and cupcakes are available, the brilliance of Jennivee’s is its rotating selection of delectable, exquisite edible art. Feast on a sky-high slice of purple-velvet ube cake with young coconut and ube mousse, or try a modern take on the classic hummingbird cake. Homemade cookies and bars are also available. Best of all, Jennivee’s is open late, so you can indulge your late-night cravings while you’re out on the town.
On the east side of Chicago’s downtown, you’ll find a segment commonly called the Museum Campus with some of Chicago’s cultural gems, including the Shedd Aquarium, the Adler Planetarium, and the Field Museum of Natural History. It’s also near the world-famous Art Institute of Chicago. If museums are your thing, there are even more options throughout the city to cater to all kinds of interests. Unless you’re planning to move here, though, you probably won’t manage to see all of them before you return home. No worries — there’s always a next time.
Nature may not be the first thing you think of when you consider Chicago, but the Garfield Park Conservatory may just change your mind. Visitors can explore indoor and outdoor gardens including thousands of plant species from all over the globe. The conservatory also offers space if you want an interesting place to host an event while you’re in town.
Liquor stores within the city limits have ceased sales after 11 p.m., though restaurants may continue to serve alcohol to vaccinated patrons later. Masks are required on planes, busses, trains, and all forms of public transportation into and out of Chicago, as per the most recent CDC recommendations, and regardless of vaccination status. Additionally, Chicago requires that masks be worn in all indoor public settings, also regardless of vaccination status.
As of September 27, Chicago’s weekly COVID-19 travel advisory included 48 states and three US territories, meaning unvaccinated travelers coming from them should be tested for COVID-19 both before and after traveling and quarantine themselves after arriving in Chicago. Since Chicago updates this travel advisory weekly, check the city’s status as close to your trip as you can. You may also want to check while you’re visiting so you can stay on top of the latest guidance.