3 Day Chicago Itinerary

3 Days in Chicago Itinerary: The Ultimate First-Timer’s Guide

Chicago, the jewel of the Midwest, is a city that never fails to amaze first-time visitors. From its stunning architecture to world-class museums and incredible food scene, the Windy City offers something for everyone.

I recently visited during MEA (Minnesota Educators’ Academy) with my family. We got exceptionally lucky to be able to spend time there during the week this time. Normally when I’ve gone, it would be a weekend trip. Now that I’ve got kids of my own, this fall break make it the perfect time to share the city with them. I’m excited to share our experiences and tips for making the most of your Chicago adventure.

Here is what I recommend for a three day adventure in Chicago without overdoing it!

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Before You Go: Essential Planning Tips for Chicago

Getting There

There are three main ways to reach Chicago, each with its own advantages:

  1. By Air: The fastest option, with flights landing at either O’Hare or Midway airports. Both airports offer direct transportation to the Loop (Chicago’s central business district). From Minneapolis, it’s just a quick hour and a half-long flight, and you can often find great deals.
  2. By Train: The recently opened Amtrak service from St. Paul offers a stress-free journey direct to Chicago. The 7.5 hour trip through Wisconsin provides scenic views and comfortable travel.
  3. By Car: A 7-hour drive from Minneapolis gives you flexibility and can be the most economical option for families. Just keep in mind you’ll need to figure out parking once you arrive.
Downtown Chicago Illinois

Where to Stay in Chicago

The Loop is your best bet for a first visit. It puts you within walking distance of major attractions and provides easy access to the “L” train system for reaching further destinations. You can also easily access bike rentals and taxis from here.

We stayed in the Hampton Inn & Suites Chicago-Downtown in Chicago. It was blocks away from the river and Michigan Avenue. We could walk to almost everywhere and when we couldn’t, the most we paid was $18 to get someplace.

Day 1: City Introduction

Afternoon: Millennium Park & The Loop

Millennium Park Highlights (1-2 hours)

The second most photographed spot in Chicago (according to Instagram) is a must-visit. The iconic Cloud Gate (aka “The Bean”) is just the beginning. Don’t miss:

  • Crown Fountain: Interactive digital art displays featuring Chicago residents’ faces
  • Lurie Garden: A peaceful 4-season garden offering a quiet escape
  • Jay Pritzker Pavilion: An outdoor amphitheater hosting free concerts and events
Millenium Park in Chicago

Art Institute of Chicago (2-3 hours)

This world-class museum houses an incredible collection of masterpieces, including:

  • Georges Seurat’s “A Sunday on La Grande Jatte”
  • Vincent van Gogh’s self-portrait
  • Grant Wood’s “American Gothic”

Pro tip: Visit on Thursdays when they’re open until 8 PM; otherwise, plan around their 5 PM closing time.

American Gothic at the Art Institute of Chicago

Nearby Bonus Activities:

  • Route 66 Starting Point: Snap a photo at the historic marker where America’s most famous highway begins
  • Chicago Cultural Center: A stunning architectural gem offering free cultural exhibits
  • Maggie Daley Park: An elaborate playground and recreation area perfect for families
  • Grant Park: Chicago’s “front yard” with beautiful gardens and open spaces
  • Harold Washington Library: Worth visiting for its stunning winter garden atrium
  • State Street Shopping: Historic shopping district with flagship department stores

Evening: Entertainment

Blue Man Group

For a unique theater experience that won’t break the bank, the Blue Man Group delivers entertainment for all ages. Their dedicated theater in Chicago offers an unforgettable interactive show. The Blue Man Group have their own theatre in Chicago.

Spring for the “poncho section” tickets if you want to be part of the action! We let my kids sit in the first row, and they haven’t stopped talking about it.

Dinner Recommendation

Before the show, head to Wilma’s for outstanding BBQ. Their melt-in-your-mouth pork tips and creative takes on Southern classics like Chicken and Waffles make it a standout choice.

Nearby Bonus Activities:

  • Lincoln Park: A charming neighborhood worth exploring with historic buildings and cafes
  • Briar Street Theatre Area: Vibrant entertainment district with plenty of pre/post-show options
  • Local Dessert Spots: Try Sweet Mandy B’s for amazing cupcakes and nostalgic treats

Day 2: Museum Campus

Chicago’s Museum Campus is a treasure trove of learning and entertainment. You can visit three world-class institutions all in one location: the Shedd Aquarium, Field Museum, and Adler Planetarium. While ambitious visitors might tackle all three in a day, I recommend choosing two to avoid museum fatigue.

Morning: Marine Life

Shedd Aquarium (2-3 hours)

Here’s an insider’s strategy to make the most of your visit: Arrive early when the animals are most active and still enjoying breakfast. The current construction has visitors entering from the Museum Campus side, which actually works in our favor for the perfect route through the exhibits.

Start your journey at the stingray touch pool – it’s free and sets the tone for an interactive experience. Then head straight to the beluga whales. Trust me, seeing these magnificent creatures underwater is breathtaking. You might also catch sight of the Pacific White-sided Dolphins in the same area – they’re absolutely stunning.

Pro Tips for getting through everything:

  • Aim to reach the shark exhibit before 10:30 AM on weekdays (that’s when school groups typically arrive)
  • Plan for the first animal show of the day in the main aquarium
  • Visit the electric eels, and octopus, exhibits after the main show
  • School groups start heading home around 2 PM if you prefer a quieter experience

For lunch, the aquarium’s cafeteria surprisingly serves some of the best museum food I’ve had. Budget-conscious visitors should check out the food trucks outside the main entrance for tasty alternatives.

Shed Aquarium

Nearby Bonus Activities:

  • Adler Planetarium: America’s first planetarium offers spectacular lake views and space exploration exhibits
  • Lakefront Trail: Take a morning walk along Lake Michigan for stunning city views
  • 12th Street Beach: A hidden gem beach right behind the Adler Planetarium
  • Museum Campus Gardens: Beautiful landscaping perfect for photos or a picnic

Afternoon: Natural History

Field Museum (2-3 hours)

Home to SUE, the largest and most complete T-Rex skeleton ever found, the Field Museum is a natural history lover’s paradise. My son was particularly excited to see the Great Auk Bird skeleton he had just studied in school.

The Egyptian collection was the biggest surprise for me. Beyond the multiple mummies on display, you can walk through a recreated tomb of Unis-Ankh, complete with original hieroglyphic walls. It’s an experience that truly transports you.

While the museum offers special paid exhibits and 3D movies, the permanent collection is more than enough to fill your afternoon. Since there’s no timed entry, you can take your time exploring.

Pro Tip: Schedule a 3D movie between your aquarium and Field Museum visits – it’s a perfect way to rest your feet and avoid museum fatigue.

Museum of Natural History in Chicago

Nearby Bonus Activities:

  • Soldier Field: Historic home of the Chicago Bears with impressive architecture
  • Northerly Island: Former airport turned nature area with great skyline views
  • Prairie Avenue Historic District: Preserved mansions from Chicago’s Gilded Age

Evening: Chicago Food Scene

No visit to Chicago is complete without trying deep dish pizza, but choosing where to go can be controversial! Here’s my insider’s guide to the great pizza debate:

  • Giordano’s: While good, it’s now available in many cities including Minneapolis
  • Pizzeria Uno: Claims to be the original, with multiple downtown locations
  • Pizzeria Due: Split from Uno (rumor has it two brothers parted ways), similar recipe
  • Pequod’s Pizza: The local favorite, about 20 minutes from downtown

My recommendation? Make the trek to Pequod’s. Why travel 400 miles to eat something you can get at home? Plus, the tourist-centered Uno/Due locations can be a bit bland.

Essential Pizza Tips:

  • Make reservations if possible
  • If you can’t get a reservation, they’ll let you order while waiting for a table
  • Plan for a 40-minute cooking time
  • Expect a line (it’s worth it!)

Day 3: Views & Shopping

Morning: River & Architecture

Architecture Boat Tour

One of Chicago’s must-do experiences is the architecture boat tour. We chose Wendella Boats, and I highly recommend booking an early morning tour when the boats are less crowded for better views and photos.

The 75-minute tour takes you along the Chicago River’s main branch, north branch, and south branch. Our guide focused on one side of the river at a time, which made it easy to follow along. You’ll see architectural marvels from Gothic to ultra-modern, including:

  • The iconic Willis Tower (formerly Sears Tower)
  • The distinctive corn-cob shapes of Marina City
  • The stunning Wrigley Building
  • The neo-Gothic Tribune Tower
  • The sleek 150 North Riverside that seems to defy gravity

Pro Tip: After the tour, head to Bongiorno’s Cucina Italiana & Pizzeria. Their authentic Italian Beef Sandwiches are incredible, and I had the best Tiramisu of my life there – possibly my favorite meal of the entire trip!

Chicago River Boat Tour

Nearby Bonus Activities:

  • River Walk: A beautiful pedestrian pathway along the Chicago River with cafes and art installations
  • Marina City: Get up close to these iconic “corn cob” towers
  • Merchandise Mart: One of the world’s largest commercial buildings with a fascinating art deco design
  • Hidden Gardens: Several buildings along the river hide beautiful public plaza gardens

Afternoon: City Views & Shopping

360 Chicago

Located on the 94th floor of the John Hancock Building, 360 Chicago offers breathtaking views of the city. On clear days, you can see across Lake Michigan and into Indiana, Wisconsin, and Michigan (though spotting state lines is admittedly tricky!).

The observation deck includes:

  • The TILT experience: A glass enclosure that tilts you out over Michigan Avenue (call ahead to confirm availability)
  • A bar with spectacular views
  • The Cloud Deck, an open-air section where you can feel Chicago’s famous breezes
  • Interactive displays about the city’s architecture

Pro Tip: Visit just before sunset to experience both daytime and nighttime views for the price of one ticket.

360 Chicago

Magnificent Mile Exploration

Known officially as North Michigan Avenue, the Magnificent Mile earned its nickname from real estate developer Arthur Rubloff in the 1940s. This upscale shopping district features:

  • Luxury retailers: Tiffany & Co., Bloomingdale’s, Saks Fifth Avenue
  • Popular brands: Nike, Apple, Zara
  • Local experiences: The Hershey’s Store, Garrett Popcorn Shop
  • Water Tower Place mall for family-friendly shopping

Nearby Bonus Activities:

  • Museum of Contemporary Art: Cutting-edge exhibits in a beautiful space
  • Oak Street Beach: Urban beach with stunning skyline views
  • Holy Name Cathedral: Historic Gothic Revival church
  • Nutella Café: Unique dessert spot dedicated to the famous hazelnut spread
  • Parlor Pizza Bar: Great spot for a casual dinner with excellent people-watching
Walking the Magnificent Mile in Chicago

Additional Planning Resources

Getting Around

Chicago is surprisingly walkable, but when you need to cover more ground:

  • Try the Divvy bike-share program for 30-minute rides between stations
  • Use the Curb app for taxis – often cheaper than rideshare services and readily available
  • Skip driving in the city if possible – parking is expensive and traffic can be frustrating

Money-Saving Tips

Museum Free Days

While most free days are reserved for Illinois residents, these museums are free to everyone:

  • National Museum of Mexican Art
  • National Museum of Puerto Rican Arts & Culture
  • Museum of Contemporary Photography
  • Smart Museum of Art
  • Hyde Park Art Center
  • Jane Addams Hull-House Museum

CityPASS

The Chicago CityPASS is valid for 9 days and includes:

  • Guaranteed admission to Shedd Aquarium and Skydeck Chicago
  • Choice of 3 additional attractions from:
    • Architecture River Tour
    • Field Museum
    • 360 CHICAGO
    • Museum of Science and Industry
    • Art Institute of Chicago
    • Adler Planetarium

Free Attractions

  • Navy Pier: Entertainment complex with free admission
  • Lincoln Park Zoo: One of the oldest zoos in North America
  • Cultural Center: Beautiful architecture and free exhibitions
  • Millennium Park: Year-round free programming

Weather Contingency Plans

Despite its “Windy City” nickname (which actually refers to its long-winded politicians rather than weather), Chicago doesn’t rank among America’s windiest cities. However, Lake Michigan can bring unpredictable weather. If rain interrupts your plans:

  • Explore the Pedway system connecting downtown buildings
  • Visit indoor attractions like the Art Institute or Field Museum
  • Shop at Water Tower Place or State Street stores
  • Enjoy a long lunch at one of Chicago’s famous restaurants

Final Tips & Tricks

Best Photo Spots

  • North Avenue Beach for skyline shots
  • Adler Planetarium for sunrise city views
  • The Bean at dawn for crowd-free reflections
  • Chicago River bridges during golden hour
  • The view from Cindy’s rooftop bar

Local Etiquette

  • Walk single file or two abreast on busy sidewalks
  • Observe traffic signals (unlike some other cities, jaywalking isn’t common here)
  • Never, ever put ketchup on a Chicago hot dog!

Seasonal Considerations

  • Summer (June-August): Peak tourist season with festivals and beach activities
  • Fall (September-November): Mild weather and beautiful colors
  • Winter (December-February): Fewer crowds but cold temperatures
  • Spring (March-May): Gradually warming temperatures and emerging gardens

Remember, every season in Chicago has its charm. Summer brings crowds but also free concerts and festivals. Fall offers perfect walking weather and beautiful colors. Winter showcases holiday decorations and smaller crowds. Spring brings blooming gardens and fresh energy to the city.

Whether you’re visiting for a long weekend or an extended stay, Chicago’s blend of culture, architecture, food, and Midwestern hospitality makes it an unforgettable destination. Just remember to pack comfortable walking shoes – you’ll need them!

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