Skip to content

Essential Travel Tips For When You Visit Chicago

visit chicago

Chicago. Photo courtesy of Patrick Emerson via flickr.

Guest post by Hailey Robinson Whether it’s your first time traveling through “The Windy City” or a familiar stop on every one of your road trips, a visit to Chicago is well worth it and easy to plan. From famous art in Millennium Park to gorgeous lakefront views and some of the finest dining in the country, get ready to enjoy the very best when you visit Chicago with these tips.

1. Travel By “L”

Chicago‘s public transportation is much more than scenic — hop aboard the Brown Line and see what it’s all about. You’ll want your camera ready as you cross over the Chicago River; it’s a convenient and affordable way to see the city. The “L” will get you around quickly for a self-guided tour of bustling Chicago, and unlike many major cities, one fare lets you transfer twice in a two-hour period. The Blue and Red Lines operate 24 hours a day with service between the North and South Sides — perfect for late night adventures.

2. Be An Urban Explorer

Who says outdoor exploration is just for nature and hiking? Chicago’s city landscape is its own exciting venture. Millennium Park is home to the iconic “Bean” as well as fountains, gardens and an outdoor beer garden at the Park Grill. For some real city action, hop on the train and head to the heart of the business district: The Loop. You’ll easily spot the Willis (Sears) Tower and enjoy other surrounding architecture and busy comings and goings. Hunting for shoes or other clothing? Swing by Michigan Avenue, Chicago’s nearly mile-long shopping street. Another must-see is the bustling and beautiful lakefront. Rent a bike and ride along Navy Pier, stopping to enjoy drinks and dining on North Avenue Beach.

3. See The Neighborhoods

Travel out into one of Chicago’s many surrounding neighborhoods and you’ll see why Chicagoans love their city so much. You’ll get a real feel for the city and its people by visiting areas like Lincoln Square, offering a traditional German dining hall and other eclectic restaurants, boutiques and bars. Visit Andersonville, a neighborhood boasting a variety of independent, locally owned businesses, for an experience in local culture. If relaxing and people-watching is your thing, consider a visit Irving Park for lake views, park walks and gorgeous old homes.

4. Savor Creative Eats

Chicago boasts some of the country’s best restaurants and food options. Try Lou Malnati’s Pizzeria, a local favorite for Chicago-style deep dish pizza with three full-service locations throughout the city. For fine and innovative dining, try Alinea Restaurant, which has been named the No. 1 restaurant in North America — or their Aviary cocktail bar, with creations that bridge science and art. Moto Restaurant has a unique tasting menu you won’t find in your average restaurant, with just as much theater involved as cooking.

5. Get Weird

While I’m not saying visit Chicago and skip the top attractions, there are a number of quirky experiences that can liven up your itinerary. Check out some of the city’s offbeat museums, like INTUIT – The Center for Intuitive and Outsider Art focused on vision-driven works from self-taught artists; the International Museum of Surgical Science; and the McDonald’s Museum modeled after a 1950s store featuring vintage equipment. Take a photo in front of Sh*t Fountain — which features a sculpture depicting a pile of dog crap, created by Polish artist Jerzy S. Kenar in protest of the animal feces consistently sitting outside his home. Another fountain worth checking out is the thought-provoking Fountain of Time, created by sculptor Lorado Taft in Washington Park — although don’t miss Oz Park, with its Wizard of Oz character statues. For a unique shopping experience, the Secret Agent Supply Co. sells spy-themed goods, with profits benefiting the adjacent 826CHI Nonprofit Writing & Tutoring Center.

Have any tips to add for those planning to visit Chicago? Please share in the comments below.

Also Check Out:

ProBlogging 101 Where To Get Chicago’s Best Pizza A Look At My Favorite Unpretentious NYC Restaurants  
Jessie Festa standing in front of grafitti wall

Hi, I’m Jessie on a journey!

I'm a conscious solo traveler on a mission to take you beyond the guidebook to inspire you to live your best life through travel. Come join me!

Blogging Courses

Want to live your best life through travel?

Subscribe for FREE access to my library of fun blogging worksheets and learn how to get paid to travel more!

.

Leave a Comment