What to do in Chicago while house and pet sitting

Known for its impressive architecture, exciting music and rich cultural and arts scene, Chicago, on the scenic shores of Lake Michigan, offers plenty of fabulous sights and activities to keep you happily busy during your pet sitting trip there.

So, if you’re in town right now and wondering what to do in Chicago today, have a look at our top suggestions below!

Chicago attractions

No matter if you’re into art, music, natural escapes or history, there is plenty of stuff to do in Chicago. For starters, let us introduce you to some of the city’s most iconic attractions:

1. The Art Institute of Chicago: an absolute must-do in Chicago for any creatively interested person is a trip to the Art Institute of Chicago, which serves as an academic institution as much as a top-notch art museum. Here, you can find about 300,000 exhibits from all over the world, including paintings, sculptures, photos, textiles, prints and more. On top of that, the Art Institute hosts more than 30 temporary exhibitions per year, making the museum an exciting experience during every Chicago trip, even if you’ve already been there before.

2. The Field Museum of Natural History: if art isn’t your thing, but you’re into science and natural history, head over to the Field Museum of Natural History and marvel at the more than 24 million specimens and other objects the museum holds, including dinosaur skeletons, fossils, gems, meteorites, anthropological pieces and cultural artifacts from all around the world.

3. Willis Tower & Skydeck Chicago: for a literally different perspective of Chicago, visit the city’s tallest building, the spectacular Willis Tower. There, you can ride up to its impressive Skydeck, an educational experience and observation deck, teaching you about the tower and offering incredible views over the city from a height of 1,353 feet, which makes the Skydeck the highest observation deck in the entire US – and a definitive contender for one of the top things to do in Chicago.

Free things to do in Chicago

If you’re in the mood for more cool things to do in Chicago but on a slightly tight budget, fret not and have a look at these things to see in Chicago:

1. Garfield Park Conservatory: offering free admission, scenic outdoor gardens, a tropical Palm House and a spectacular Desert House, a Horticulture Hall and much more, the Garfield Park Conservatory is the place to be in Chicago for any nature lover. And if walking through the lush gardens isn’t enough relaxation for you, you can also partake in special events like Yoga sessions or transformative dance classes.

2. Grant Park, Millennium Park & Buckingham Fountain: spanning 319 acres, Grant Park is more than just one park but actually comprises several parks and other areas, including Chicago’s Millennium Park and its fascinating art installations, Museum Park – home to five museums –, and the beautiful Buckingham Fountain. Dogs on a leash are welcome in most of Grant Park, too, and there’s even a designated off-leash area.

3. The Magnificent Mile: to take a look at some of Chicago’s most iconic buildings, take a walk down the city’s ‘Magnificent Mile’, the impressive avenue stretching from Michigan Avenue at the Chicago River all the way to Lake Shore Drive. Some of the most famous landmarks along the Mile are the historic Chicago Water Tower, Tribune Tower and the statue of Abraham Lincoln nearby, the Wrigley Building and the John Hancock Center.

Fun things to do in Chicago

Are you in the mood for a fun, relaxed afternoon? And does it make you wonder: “What are the best things to do in Chicago today?” We’ve got you covered:

1. Navy Pier: if you’re into rides, amusement and yummy food, Chicago’s Navy Pier is your place to be. The exciting waterfront area offers a ferris wheel and other attractions, exhibitions, parks, gardens and a plethora of bars, restaurants and food stalls to satisfy any munchy cravings you might have.

2. American Writers Museum: if you love literature, a visit at the American Writers Museum should most definitely be on your Chicago bucket list. Modern and interactive, the museum focuses on the history of American literature and its creators and features permanent as well as temporary exhibits catering to all literary tastes and age groups.

3. Live Music: Chicago loves music, from pop, rock and hip hop to punk, blues and jazz. It therefore comes as no surprise that you can also find plenty of live music venues throughout the city, from small and intimate to huge and spectacular, offering opportunities to enjoy live performances literally every day of the year, should you wish so. 

What to do in Chicago with pets

If you’re sitting a dog and would like to go on adventures with the pooch, too, here are some fun things to do in Chicago you two can enjoy together:

1. Chicago Lakefront Trail: for some scenic river vistas and relaxing walks with your new four-legged friend – albeit on a leash – take a trip to the Chicago Lakefront Trail. The 18.5-mile walkway takes you past all four of the city’s major lakefront parks as well as various beaches, and can be enjoyed on foot, bike or skates.

2. Montrose Dog Beach: fancy a trip to the beach? Not every beach in Chicago allows for dogs, but the Montrose Dog Beach most definitely does – and it’s stunningly beautiful, too. The fenced area is operated by the volunteers of the MonDog organization and offers free, safe, off-leash fun for you and your furry buddy.

3. Oz Park: if you love the Wizard of Oz or fantastic adventures in general, grab Toto and head over to Oz Park. The fun themed park comes with cute statues of all the major characters of the book, an exciting playground for kids, lush meadows for long, relaxing walks and the blooming Emerald Garden. Oh, and of course, you can also lie in the grass here and read a book, if you like – unless there’s a tornado warning.

Or, for more ideas, check out this list of the best dog parks in Chicago.

Best Restaurants in Chicago: Food and drink

Got the munchies after all the sightseeing and cultural outings? No problem, here are some of the best restaurants in downtown Chicago and other parts of the city:

1. River Shannon: dog-friendly, cosy, and serving amazing food and drinks, the River Shannon Irish pub is the perfect place for a relaxing, fun evening out, meeting new people or simply enjoying a yummy dinner. And if you’re in for a walk afterwards, it’s also really close to Lincoln Park and the North Avenue Beach.

2. La Scarola: craving pasta? This homely, atmospheric little eatery happens to be one of the best Italian restaurants in Chicago, serving anything from delicious comfort food to fancy meat dishes. The prices are on the medium to high end, but the offer is worth the bill.

3. Oriole: if you’re in for a truly unique dining experience and are willing to ignore the price tag to do so, plan for a dinner at Oriole, a beautiful, high-end, New American eatery, serving fancy tasting menus and a selection of vintage wines. Delicious, exciting, but definitely pricey.

Are you all set for your pet sitting adventures in Chicago now? The wonderful city on Lake Michigan’s shores offers much more than what we’ve covered in this article and is best experienced in person – so head over to our currently available sits and find Chicago owners and their pets so you can start your journey as soon as possible. And in the meantime, why not have a look at our blog to get some more inspiration for exciting pet sitting trips all around the world?

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