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How To Plan a Solo Trip to Chicago

December 1, 2023 By CityPASS

With its eclectic mix of modern and historic architecture, world-class art, and iconic foods, Chicago is an exhilarating destination for solo travelers. Whether you're looking to immerse yourself in culture, savor culinary delights, or simply wander amid the city's iconic skyscrapers, a solo trip to the Windy City promises a buffet of enriching experiences.

Why Should You Travel to Chicago By Yourself?

Solo travel allows complete immersion into a city at your own pace. Chicago is ideal for solo travel with friendly locals, walkable neighborhoods, and endless attractions catering to every interest. The freedom of planning your own schedule, coupled with the vibrancy of this Midwest metropolis, creates an unforgettable adventure.

Traveling to Chicago alone lets you encounter the city's sights through your own lens, whether appreciating world-famous artwork up close, indulging in local cuisine, or admiring magnificent architecture. Each day offers new neighborhoods to explore, from bustling downtown to trendy music enclaves. With Lake Michigan beaches and tranquil parks providing natural escapes from urban energy, Chicago nourishes mind, body, and spirit.

Some key advantages of visiting Chicago by yourself include:

  • Total freedom to customize your itinerary based on personal interests
  • More opportunities for spontaneous adventures
  • A sense of confidence in navigating a new place solo
  • Moments of introspection while experiencing sites without distraction
  • Leisurely pacing for photographs that captures the essence of places
  • Fulfilling days bookended by long café sits and neighborhood wanders

Top 7 Things To Do by Yourself in Chicago

Here are the best ways to enjoy a trip to the Windy City when you're the only one calling the shots:

1. Enjoy a Mouth-Watering Chicago-Style Pizza

No food encapsulates Chicago better than deep dish pizza, with its thick crust holding generous layers of cheese and toppings. Lou Malnati's iconic recipes taste just as delicious in their downtown location as at the original Lincolnwood pizzeria. Or try Gino's East, which has also stood the test of time, baking hand-pressed crusts since 1966. Their secret spice blend takes taste buds on a trip to flavortown. Devouring Chicago pizza solo lets you savor every bite.

2. View Great Impressionists at the Art Institute of Chicago

The Art Institute's peaceful galleries make art absorption contemplative. Stand inches from vivid textures and brush strokes without distractions.

Founded in 1879, the Art Institute of Chicago houses one of the world's great art collections. The Museum's impressionist and post-impressionist pieces alone are jaw-dropping. Spend hours getting lost in Monet's dreamy, light-filled landscapes and absorbing the colorful swirls of Van Gogh's greatest works. The vibrant colors and movement of Seurat's pointillism pieces are even more striking up close. Without companions rushing you along, you can get lost in the masters' creations. Don't forget to snap some solo pics out front with the Art Institute's iconic bronze lion sentinels.

3. Travel 4.6 Billion Years to the Past at the Field Museum

This lakefront natural history museum holds fascinating treasures, from sparkling gems to massive dinosaur skeletons like SUE, the most complete T-rex ever discovered.

At the immense Field Museum, exhibits transport you through over 4 billion years of history and back to when massive megafauna ruled the Earth. Ponder ancient burial rituals while examining remarkably preserved Egyptian mummies. Meteorites and huge dinosaur skeletons fill the halls. With so much to explore, you can spend hours examining each exhibit's details.

4. Discover the Shoreline Sightseeing Architecture River Tour

This boat tour along the Chicago River provides an unparalleled view of the city's world-famous skyline from below. While you float, guides expertly narrate the jaw-dropping sights surrounding you. Over 50 architecturally important buildings pass by, representing Chicago's history of creative design prowess. See late 19th and early 20th century early skyscrapers, like the neo-Gothic Wrigley Building. Contrast those with the city's mid-century modern glass-and-steel towers, culminating in contemporary feats like the 110-story Willis Tower. Without other tourists bumping your elbow, you can snap countless stellar photos to remember this remarkable sightseeing experience.

5. Connect With Nature at Millennium Park

In the heart of Chicago's concrete jungle, the oasis of Millennium Park provides a refreshing escape into nature and public art. This downtown green space nourishes the soul between urban explorations. Designed to celebrate the turn of the millennium, the park's gorgeous gardens, modern sculptures, and pavilions offer a perfect spot for solo relaxation. The futuristic Jay Pritzker Pavilion's steel ribbons form a geometric work of art. Linger in the Lurie Garden's tranquil setting, then head to the iconic Cloud Gate sculpture, "The Bean," for its reflective kidney-bean shape. Snap selfies on its mirrored surface, then sprawl on the grass to enjoy a picnic lunch while staring up at the city's magnificent towers.

6. Meet the Marine Animals at Shedd Aquarium

At Chicago's lakefront Shedd Aquarium, you'll come face-to-face with thousands of fascinating aquatic creatures, spanning from playful penguins to menacing piranhas. Enter the outstanding Abbott Oceanarium habitat to wander alongside a Pacific coral reef setting alive with sleek sharks, rays, and rainbow-hued fish. Don't miss the chance to pet stingrays gliding by in the Waters of the World exhibit. The aquarium's special effects 4-D cinema adds multisensory elements like wind and mist to make you feel part of the onscreen marine action.

7. Experience Jaw-Dropping Views at Skydeck Chicago

Nothing matches going to the top of the third tallest building in the Western Hemisphere for panoramas of Chicago and its surrounding states. At Skydeck Chicago on the 103rd floor of Willis Tower, glass boxes let you step out and literally stand over the city 1,353 feet below. Feel the adrenaline rush through your veins as clouds drift by around you. Peer straight to the ground in thrilling views. Pose for unique outward-facing photos on The Ledge's glass balcony jutting out from the tower. The 360° views of Chicago's sprawl let you fully appreciate the city's grandeur in solitary wonder.

Experience Everything the Windy City Has To Offer With CityPASS® Tickets

Chicago has many incredible museums, exhibits, tours, and sightseeing opportunities, and we're here to make seeing the city's premier attractions simple and affordable. CityPASS® tickets offer big savings on famous things to do in Chicago. For solo travelers seeking to optimize their itinerary, it's an easy way to knock out bucket list sites. Then, you can concentrate on finding Chicago's hidden local gems at your own pace.

Chicago Lodging

To get the most out of your stay in Chicago, we recommend finding lodging near Chicago's top attractions. Use this map to find the right lodging for you:

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