Windy City Weekend in Chicago

We’ll admit, a long weekend may not nearly be enough time to wind your way through the incredibly diverse attractions, sites and neighborhoods of the wonderful Windy City. But the good news is that you will tick off many To Do list items – and enjoy some incredible food – with the help of our handy guide and tips for visiting Chicago.

Five things you must see and do

1. Take an Architecture River Tour: The devastating Chicago Fire of 1871 may have burned the downtown to the ground. But from its ashes rose a city skyline and architectural landmarks that are unrivaled in the United States. A Shoreline Sightseeing Architecture River tour on the Chicago River is the best way to view and understand how one hundred years of architectural styles and buildings came to be. An expert guide leads the 75-minute tour, and explains the history of how Chicago’s buildings, architecture and engineering made its landmarks and the city famous.

2. Art Institute of Chicago: Founded in 1879, the Art Institute of Chicago is one of the oldest art museums in the United States, with the largest collection of Impressionist and Post-Impressionist art outside the Louvre. There are more than 300,000 pieces of art to view, so take your time and wear comfy shoes. Kids can design and print their own custom Journeymaker guides. View ancient Etruscan pottery and Greek reliefs or focus on modern art like Pablo Picasso’s The Guitarist. And don’t miss the Thorne Miniature Room, filled with tiny rooms fashioned on real interiors from churches to tudor castles to one of Frank Lloyd Wright’s houses.

3. Navy Pier: When visiting Chicago, it’s impossible not to visit Historic Navy Pier. Fun for visitors and locals alike, Navy Pier hosts events throughout the year, as well as fun attractions like the Amazing Chicago Funhouse Maze and Centennial Wheel. Take a food tour or stop in to enjoy one of the many restaurants located in this vibrant entertainment district.

4. Field Museum: Take a journey of discovery at the Field Museum. This natural history museum caters to dinosaur lovers and everyone interested in the connectivity of our planet’s ecosystems and cultures. Maximo, the museum’s newest resident titanosaur, is one of the largest dinosaur fossils ever found, much less put on display.

5. The Chicago Bean: Properly known as Cloud Gate, the Bean is an impressive public art structure has become iconic with the city. Locals and visitors love seeing their reflections in, and taking selfies with, the reflective Bean sculpture. It’s one of the highlights of Millennium Park, which also includes the fun and interactive Crown Fountain. Tip: This is a great place to cool off in summer.

Where to Eat in Chicago

There are so many places to eat a fabulous meal in Chicago. It’s a foodie paradise. Here are some favourites:

Terzo Piano – A refined, beautifully designed and family-friendly lunch or dinner spot in the Modern Wing of the Art Institute of Chicago.

DMK Burger Bar – Fantastic burgers and fries at Navy Pier and around the city.

Ozzie Pops and Pretzels – Take a break with a seasonal, all-natural popsicle, hand-twisted pretzel or fresh squeezed lemonade at Navy Pier Family Pavilion.

Chromium – Farm to table, healthy, and seasonally-inspired American cuisine at Hotel Midtown.

Gino’s East – Classic, deep dish Chicago pizza. Variety of locations. Deep dish newbie? Note that it takes about 45 minutes to prepare one of these filling pies. It is worth the wait.

Eduardo’s Enoteca – In Chicago’s Gold Coast, a classic Italian neighborhood eatery with rustic pizzas and handmade pastas.

Best Candy Store

Shop local at the sweetest destination in the city, Candyality. Give in to your sweet tooth cravings for sour candies, Jelly Belly beans, speciality licorice or imported treats from Britain and Japan. Ask for a special Candy Personality reading to understand what your candy choices say about you.

Where to Stay

The Hotel at Midtown caters to active travelers who want to balance good food and a good time, without sacrificing fitness or their healthy lifestyle on the road. Located in the city’s revitalized Bucktown neighborhood, this boutique hotel property is also a full-service athletic and sports resort. Hotel guests can take advantage of all of the property’s wellness offerings, which include two pools, tennis courts, boxing gym, workout classes, cycle and yoga studios, and golf simulators. The new suites are spacious and simply designed with real hardwood floors and lots of natural light.

Stop in for a lunch or dinner at Chromium, the in-house restaurant. It specializes in farm-to-table fare with lots of locally sourced produce, and many items like mayonnaise, mustard and even soft-serve ice cream made from scratch. The food is fresh and delicious, with gluten and vegan options available, and the restaurant is very family-friendly.

Where to go for a night out

You many not know exactly what you’re in for, but an evening with the Blue Man Group may well blow your mind. Leave your expectations at the door and let three bald and blue men take you on a journey rocking with music, laughter and surprises. In the words of a pint-sized critic, ‘that was sensational!’.

Disclosure: The writer thanks Choose Chicago for hosting her stay and visit. As always, her opinions are honest and her own.

Claudia Laroye is a travel writer and editor based in Vancouver, Canada. An avid and curious traveler, Claudia has written about family, adventure, and luxury experiences for local and national publications since 2010. Claudia is the Contributing Editor of Twist Travel Magazine, and has written for WestJet Magazine, Lonely Planet, Fodor’s, Travelzoo, Westworld, Family Fun Canada, Travel Mamas and Dreamscapes magazine. She is the founder of family travel site The Travelling Mom. You can find her on Instagram at @thetravellingmom.

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