Summer in Chicago

This article originally appeared in the August 2017 issue of So Scottsdale! magazine.

Chicago might be known as the “Windy City” with long, cold winters, but its summers are delightful, with pleasant weather (maximum temperatures are in the 80s) ad festivals and fun aplenty. Situated on the shore of Lake Michigan, Chicago is no ordinary concrete jungle, with a whopping 552 parks and 33 beaches. It is also filled with classic architecture and luxury hotels and is home to 26 Michelin-starred restaurants. That being said, it's an ideal escape from the Arizona heat.

Art and Architecture

Chicago grew in popularity during the World's Columbian Exposition of 1893—which celebrated the 400th anniversary of Christopher Columbus' arrival int heNew World in 1492—when an estimated 150,000 people visited the city every single day for six months.

Upon arrival, they discovered a city filled with grand buildings. Experience some of this grandeur yourself by booking an architectural tour. One of the most popular tours is a 90-minute river cruise with Chicago's First Lady Cruises. You can also take a walking tour to get inside of some of these architectural gems. For example, the Historic Treasures for Culture and Commerce tour, available through the Chicago Architecture Foundation, goes inside the famous 19th-century Palmer House, and you can stand under the breathtaking dome of the original Chicago Public Library.

Of course, no visit to Chicago is complete without checking out The Art Institute of Chicago. The second-largest art museum in the country, it houses one of the best collections of impressionist paintings, including works by Claude Monet and Auguste Renoir.

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Art Institute of Chicago

Art Institute of Chicago. Photo by Susan Lanier-Graham

The modern wing of The Art Institute is a peaceful place to wander. Be sure to check out Marc Chagall's America Windows, which commemorates the American Bicentennial. They once marked the entryway to the museum, but now hang in a dedicated hallway.

Chicago by Night

After you've had a chance to take in the architectural glories of Chicago by day, head to the 360 Chicago Observation Deck high atop the John Hancock Building to get unbelievable city views at night. Located on the 94th floor (and 1,000 feet high!) you get a bird's-eye view of the city and Lake Michigan.

Chicago at Night

Chicago at Night from 360 Chicago Observation Deck. Photo by Susan Lanier-Graham

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Truly, this is a picture-perfect spot to grab a cocktail or glass of Champagne and toast the sunset. If you're looking for a bit of a thrill, check out the venue's latest attraction, TILT. Billed as Chicago's highest thrill ride (and the first of its kind worldwide), you step into a glass cube and tilt out over the city above The Magnificent Mile and the Chicago skyline.

Stay in Style

One of the places you see on a walking tour of Chicago is the Reliance Building at Washington and State streets. This National Historic Landmark was the city's first skyscraper, built in 1895 by Daniel Burnham, John Root, and Charles Atwood. The building, with its unique white terra cotta and glass facade, now houses a luxury boutique hotel, StayPineapple Chicago (formerly Hotel Burnham), which oozes Old World charm.


Reliance Building is home to The Alise Chicago. Photo by Susan Lanier-Graham

With 122 rooms in the heart of downtown, it's in an ideal home base just blocks from The Art Institute, Millennium Park, the theater district, and Michigan Avenue shopping (also known as The Magnificent Mile). The StayPineapple Chicago is also across the street from the iconic Macy's department store that was originally Marshall Field & Company.

Even after a day of exploring, there's still much to anticipate at StayPineapple Chicago, such as complimentary treats in the lobby (don't miss their signature pineapple cupcakes) and custom yellow beach cruisers to see the city in a different way.

summer in chicago

Enjoy complimentary pineapple cupcakes each afternoon at StayPineapple Chicago. Photo courtesy StayPineapple

The hotel is also dog-friendly, and you'll want to make sure you enjoy a delicious meal at the hotel's eatery, Atwood, which cooks up seasonal American food and follows the Monterey Bay Aquarium's seafood sustainability standards. (Please note: Atwood is not open during the COVID-19 pandemic. Check the website for the latest information.)

Dine Around

With the aforementioned 26 Michelin-starred restaurants, there are no qualms about it: Chicago is a foodie town indeed. James Beard Award-winning Chef Tony Mantuano is a partner in several culinary ventures that offer unique experiences, both close to The Alise Chicago.

Two concepts—Spiaggia and Café Spiaggia—are housed in the same location but offer two different dining experiences. the more casual Café Spiaggia is open for lunch and dinner, serving up handmade pasta, shared plates, pastries, and coffee. The café is a display of Italian home cooking, especially with its Sunday supper menu and family-style dining options.

summer in Chicago

Enjoy family-style dining and homemade pasta at Café Spiaggia in Chicago. Photo by Susan Lanier-Graham

For a more upscale dining experience, book a table at Spiaggia, which has garnered a Michelin star and is a recipient of numerous awards. In fact, it's consistently named one of “America's 100 Best Wine Restaurants” by Wine Enthusiast magazine, giving a nod to its 700-bottle wine list.

If you're in Chicago on a Sunday morning, head across the bridge to River Roast, where Executive Chef John Hogan puts on Blues & Brunch, pairing creative morning-time indulgences with some of Chicago's finest blues musicians performing live. Be sure to try the rabbit waffles or mascarpone French toast.

Chicago summer

Try the mascarpone French Toast at River Roast. Photo by Susan Lanier-Graham

Undoubtedly, sipping a bloody mary and listening to the blues is an ideal way to end a Chicago sojourn.

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Be sure to find more articles on Wander for what you can do when you visit Illinois.

Chicago might be known as the "Windy City" with long, cold winters, but its summers are delightful, with pleasant weather (maximum temperatures are in the 80s) ad festivals and fun aplenty. Situated on the shore of Lake Michigan, Chicago is no ordinary concrete jungle, with a whopping 552 parks and 33 beaches. It is also filled with classic architecture and luxury hotels and is home to 26 Michelin-starred restaurants.

Written by Susan Lanier-Graham

Founder and publisher Susan Lanier-Graham has traveled the world for the past twenty years, filling a passport or two along the way. She has wandered through the jungles of Thailand, explored the mysteries of the Great Pyramids, and shared the night with a leopard in Zambia. She sailed in the Mediterranean, sipped her way through Burgundy canals and Champagne caves. She followed Rembrandt’s footsteps through Amsterdam. Susan found her center on the red rocks of Sedona and soaked up an exquisite sunset over the Indian Ocean in Bali. Susan is always looking for wow moments around the world or across the street to share with adventure lovers everywhere. She has authored more than 75 books and hundreds of magazine articles. Susan is an award-winning travel writer and member of the Society of American Travel Writers (SATW) and International Food, Wine and Travel Writers Association (IFWTWA). She is a Certified California Wine Appellation Specialist (CWAS). Susan's work still regularly appears in print and online. Susan is an award-winning travel writer, a member of the Society of American Travel Writers (SATW) and is a Certified California Wine Appellation Specialist (CWAS). Susan has worked as an ambassador for Travelocity and is currently a travel ambassador for Rocky Mountaineer. Her work regularly appears in print and online in a variety of publications. These include various AAA publications, Postcards for Travel Leaders,,,, So Scottsdale, Uptown, Green Living AZ, Life Refined, Modern Luxury,, WHERE Arizona, WHERE Traveler Phoenix + Scottsdale, and more.

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