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4 Things to do in Chicago This Summer

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TPG Contributor Amber Gibson is a Chicago native and still calls The Windy City home. Here, she shares why it’s a good idea to visit this summer — you know, when it’s not frigid and snowing. Follow along with Amber’s adventures on Instagram.

It’s always a good time to visit the Windy City — well, maybe not in the dead of winter, but you know what I mean. There’s a lot going on lately, like the opening of a new and improved Navy Pier Ferris Wheel, and as always this time of year, a ton of free concerts in Millennium Park. Here are four things you should definitely do if you’re visiting Chicago this summer.

1. Visit the New Centennial Wheel at Navy Pier

A bigger and better Navy Pier Ferris Wheel — now called the Centennial Wheel — opened to the public May 27 after being closed since September for construction.

Netherlands-based company Dutch Wheels, who built Navy Pier’s old Ferris wheel, is responsible for designing and installing the new model, which holds up to 420 passengers in 42 enclosed gondolas — that’s 180 additional passengers compared to the old wheel. At nearly 200 feet high, it’s roughly 50 feet taller than its predecessor too. The two-sided cars can also withstand winds of up to 115 miles per hour, which should come in handy on gusty days.

Navy Pier Ferris Wheel. Image courtesy of Navy Pier.
A peek at the new-and-improved Centennial Wheel. Image courtesy of Navy Pier.

2. Dine in Chicago’s Hip West Loop Neighborhood

The options for incredible casual and fine dining are overwhelming in what has become Chicago’s hottest neighborhood for feasting and drinking — you could probably eat at different West Loop restaurants for lunch and dinner every day for an entire week without having a bad meal.

Start by sipping boozy slushies on the patio at Expat or some bubbly at RM Champagne Salon before walking to dinner at one of a dozen great restaurants within just a few blocks. Top Chef divas Sarah Grueneberg and Stephanie Izard recently opened Monteverde and Duck Duck Goat, respectively, both of which are excellent and exceedingly hard to get into.

If Italian-American food is more your style, try Formento’s, which serves the best meatballs and chocolate cake in town. If you’re ready to splurge, try Oriole, where a tasting menu runs $175 per person but is worth every bite.

Formento's Canestri with Sunday Gravy. Image courtesy of Choose Chicago.
Formento’s Canestri with Sunday Gravy, a fabulous dish. Image courtesy of Choose Chicago.

3. Get in Shape Outdoors

After all that eating, you’ll want to work off the calories. The 40-foot climbing wall at Maggie Daley Park Rock opened last May and features a total surface area of 19,000 square feet, able to accommodate up to 100 climbers at a time. Staff are there to assist beginners and equipment is available to rent for three different types of climbing: lead-harnessed, bouldering and top rope.

The 606 Elevated Trail is another great option for outdoor recreation if you want to bike, jog or take a leisurely stroll. The 2.7 miles of landscaped trail and four ground-level parks decorated with murals by neighborhood artists opened last year, converted from an abandoned railway.

More adventurous spirits can try taking a flying trapeze class at Belmont Harbor in Lincoln Park with TSNY Chicago.

The 606 Trail. Image courtesy of Choose Chicago.
The 606 Elevated Trail is a great way to stay in shape while exploring local neighborhoods. Image courtesy of Choose Chicago.

4. Attend an Outdoor Music Festival

Chicago has plenty of outdoor music events all summer long — and most of them are free. Pack yourself a picnic and check out a free concert at the Jay Pritzker Pavilion in Millennium Park during the free Summer Music Series each Monday and Thursday at 6:30pm through Aug. 25.

Pritzker Pavilion. Image courtesy of Choose Chicago.
The Jay Pritzker Pavilion in Millennium Park, a great venue for free shows all summer long. Image courtesy of Choose Chicago.

The Grant Park Music Festival is another great free option if you’re looking to indulge in classical concertos and symphonies — you can also learn more about the music and performers at the festival’s accompanying lecture series.

For fans of other musical genres, there’s everything from Pitchfork (July 15–17) and Lollapalooza (July 28–31) to free events like the Chicago Blues Festival (June 10–12) and Chicago Jazz Festival (September 1–4).

A Final Tip

Wondering where to stay? Book a room at the Waldorf Astoria Chicago, one of the most luxurious options in town, with rates starting at $281 or 95,000 Hilton HHonors points per night in July.

The Ritz-Carlton Chicago changed management last year and is no longer a Four Seasons property, so you can now book a room here with Marriott or Ritz-Carlton Rewards points. Rates here start at $308 or 50,000 points per night in July.

Other notable options include LondonHouse Chicago, part of Hilton’s new Curio Collection (rates from $249 or 60,000 Hilton HHonors points per night in July) and The Gwen, a Luxury Collection Hotel, part of Starwood (rates from $199 or 12,000 Starpoints per night in July).

Will you be visiting Chicago this summer? What are your favorite things to do there?

Featured image courtesy of the City of Chicago.

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