48 Hours in Chicago: a windy city weekend

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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 48 hours in Chicago.

weekend in chicago

5 things to do in 48 hours in Chicago

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, explaining the history of how Chicago’s buildings, architecture and engineering made the city famous. This tour is a must for an adult weekend in Chicago, or if you’re visiting Chicago with teens or tweens.

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.

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3. Navy Pier: When visiting Chicago with kids or without, 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.

Be sure to purchase a Chicago CityPASS to discover the best attractions on your weekend in Chicago.

weekend in chicago

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.

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.

weekend in chicago

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, Chicago Mix popcorn, 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.

weekend in chicago

Where to Stay in Chicago

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. The hotel is located in the city’s revitalized Bucktown neighborhood. The boutique property is also a full-service athletic and sports resort to help guests enjoy a full and active weekend in Chicago.

Hotel guests can take advantage of all of the property’s wellness offerings including; two pools, tennis courts, boxing gym, workout classes, cycle and yoga studios, and golf simulators.

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. Many menu items like mayonnaise, mustard and even soft-serve ice cream are 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 in Chicago

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!’.

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Disclosure: The writer thanks Choose Chicago for hosting her stay and visit. As always, her opinions about great candy and architecture are honest and her own. This article contains affiliate links. Thank you for your support.

Claudia Laroye
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2 thoughts on “48 Hours in Chicago: a windy city weekend”

  1. Pingback: Top 15 dog friendly hotels in Chicago 2020 | Boutique Travel Blog

  2. claudia, i am planning to visit chicago on february 19-21 and spent the weekend with my son 14 years old. he is in aboarding school in Oaklawn academy.
    i know that is too cold in february. where do you recomend me to stay and to do…
    thank you

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