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Chicago
The Windy City
I'd be remiss if I didn't start with my hometown of Chicago, my Kind of Town.
Why
The 3rd largest city in the US has a lot to offer. From skyscrapers to skylines, the lakefront and riverwalk, museums, sports, parks and beaches, Chicago has it all. The main sights are centrally located in the heart of downtown and the Chicago Transit Authority (CTA) transit system makes it super easy to get around.
The Why, When & How to visit...
When
With 30 miles of lakefront along Lake Michigan, Summer is the best time to visit Chicago. There's nothing like enjoying time at the beach, boat ride, or beer at a baseball game during a Summer day in Chicago. There are plenty of cold weather activities to do in Chicago too, should you decide to visit during colder months.
How
With two international airports: O'Hare (ORD) and Midway (MDW) and direct flights from most domestic and many international destinations, Chicago is easy to reach. The CTA train lines connect ORD via the Blue Line and MDW via the Orange Line making it easy and inexpensive to reach the city from the airport.
Where
to stay...
1) The Gwen - I couldn't not include my namesake hotel named after sculptress Gwen Lux, who created the facade of the building in 1928. The Gwen brings 1930s glamour back to life and always has fun, unique offerings like glamping, yoga, and even curling to utilize the outdoor terrace all year long. The restaurant offers tipsy tea, live music, and aperitivo hours certain days and times. To top it off, there's even a Moet & Chandon vending machine in the lobby to fill your champagne cravings. The Gwen is centrally located off Michigan Ave. and adjacent to a mall for a convenient shopping resting spot. Pictures and more details with the ability to book is accessible here.
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2) citizenM - One of the newest hotels in Chicago, the citizenM brand opened in Chicago in September 2022 part of a brand new 47-story tower. citizenM designs their hotels for the modern traveler with a focus on technology, sustainability, and feel. The Chicago location has a fun, modern, artistic vibe with a 2,000 sf terrace, creative meeting spaces, and living room to hang out, in addition to the restaurant and bar. Rooms have a minimalist aesthetic prioritizing value for space. The hotel is located on Michigan Ave. south of the Chicago River close to Millennium Park. Pictures and more details with the ability to book is accessible here.
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3) The Chicago Athletic Association Hotel - Dating back to 1893, the building was meticulously restored to its former glory memorializing its athletic association history with a one-of-a-kind hotel. The hotel is thoughtfully designed utilizing its athletic club history with common areas that are rich and opulent with old world charm, yet comfortable and warm with modern twists. Rooms are minimal, yet luxurious and spacious. The hotel is great year-round with its rooftop restaurant and terrace and location across from Millennium Park. It is perhaps most compelling during colder months with its cozy Drawing Room lobby, Cherry Circle Room restaurant, speakeasy, and Game Room bar. You may never want to leave. Pictures and more details with the ability to book is accessible here.
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*Looking for an apartment stay? Click here to see what chic apartments Sonder has available in Chicago.
What
Do
to...
1) Take a Boat Ride - Choose from an architectural boat ride down the river, a cruise down the lake, or water taxi to Chinatown or Museum Campus. City Experiences offers cruises departing from Navy Pier and the Chicago River front, including those with architectural tours, food and drinks to check out here.
Known for its beautiful Odyssey cruise ships, City Experiences recently added the Odyssey Chicago River boat that is one deck with floor to ceiling windows for incredible views of the Chicago skyline in a more intimate setting. There is a brunch and dinner cruise option to enjoy a meal and drinks while taking in the sights making a great experience for visitors, staycation, special occasion or group event.
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2) Explore Navy Pier - Navy Pier has a little bit of everything with restaurants, beer gardens, boat rides, hotel, theater, entertainment and events, a Ferris wheel and carousel for fun for the whole family. Navy Pier has fireworks displays every Wednesday and Saturday night during the Summer and year-round special events for the different seasons making it a year-round destination.
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3) Watch a Sporting Event - With two Major League Baseball teams: the Cubs and the White Sox, you have your choice during the baseball season.
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If visiting during colder months, visit one of Chicago's many museums mostly located in the heart of the city. The Art Institute is a staple with a Modern Wing of more contemporary pieces. Taking in a Bulls (basketball), Bears (football), or Blackhawks (hockey) game is another great option during those seasons.
Eat
Chicago has incredible and endless high-end restaurant options, but is known for its casual bites: deep dish pizza, Chicago style hot dogs, Italian beef sandwiches, popcorn, etc. Be sure to indulge in these while here.
Drink
Beer will best compliment aforementioned bites. Malort is another option as a Chicago specific herbal liquor for the adventurous types.
*If of legal drinking age.
Wear
Comfy Casual
Watch
Ferris Bueller's Day Off
by John Hughs
(showcases the city '80s style)
Listen
"My Kind of Town"
by Frank Sinatra
(this song says it all)
Gift
Click here for Gift ideas