7-Day Chicago Family Vacation Itinerary
Experience the best of Chicago with one major highlight each day, balanced with cultural sights, outdoor fun, local eats, and downtime. This itinerary is designed for a moderate pace, using public transit or Uber from a convenient downtown base.
Day 1: Welcome to Chicago – Millennium Park & The Loop

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Morning
Arrive and check into your downtown hotel. Take a leisurely walk around the neighborhood to get your bearings and grab a light lunch. Save your energy for the afternoon – this trip is a marathon, not a sprint.

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Afternoon
Explore Millennium Park, Chicago's iconic lakefront green space. Visit Cloud Gate (aka "The Bean"), the famous mirrored sculpture that reflects the skyline and park scenery – a perfect family photo spot. Watch the digital faces on the Crown Fountain spit water (the 17-year-old might get a kick out of running through the splash!). Find a bench or a patch of grass to relax and people-watch amid public art and gardens.

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Evening
Kick off your Chicago food adventures with a classic deep-dish pizza dinner. One popular spot is Giordano's (Prudential Plaza, a short walk from Millennium Park), a legendary pizzeria known for its cheese-stuffed pies. (Be prepared – it takes about 45 minutes to bake, so sip a soda and recap your day while you wait.) After dinner, enjoy a relaxed stroll through the lit-up park or along the nearby Chicago Riverwalk for lovely city views at night. Then head back to the hotel for a good night's rest.
Day 2: River Architecture Cruise & Magnificent Mile Stroll
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Morning
Ease into the day with a late breakfast. You might try Wildberry Pancakes & Cafe (near Millennium Park) for amazing pancakes and coffee, or grab a quick bite from a cafe. Afterwards, make your way to the Chicago River. Wander along the Chicago Riverwalk, a 1.25-mile waterside path with great skyline views and cafes. This is a good chance to relax by the water, watch boats, or even toss a coin in the wishing fountain.
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Afternoon
Today's big highlight is an Architecture River Cruise, a must-do for any Chicago visit. Board an afternoon tour boat on the Chicago River (departures are typically near Michigan Avenue bridge or Navy Pier). As you glide through downtown, you'll learn about Chicago's world-famous architecture – from art deco gems to modernist skyscrapers – with a breezy boat ride as your classroom. Even if you're not an architecture buff, the engaging commentary and skyline panoramas will captivate all ages. The tour lasts about 75–90 minutes. After the cruise, treat yourselves to a late lunch at Portillo's (100 W. Ontario St., about a 15-minute walk or quick Uber ride from the dock). This casual spot is just steps from the Magnificent Mile and serves Chicago specialties like the iconic hot dog and Italian beef in a 1930s gangster-themed setting. Try a fully loaded Chicago-style hot dog (no ketchup!) or an Italian beef sandwich with sweet peppers.
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Evening
Walk off your meal with a gentle stroll up Michigan Avenue, Chicago's Magnificent Mile. Peek into shops or just enjoy the buzz of the city's premier shopping boulevard. Don't miss the Historic Water Tower on Michigan & Chicago Avenue – built in 1869, it's one of the few buildings to survive the Great Chicago Fire of 1871, now a symbol of the city's resilience. As the sun starts to set, you'll see the city light up. For dinner, keep it flexible – there are countless options along the Mag Mile/River North area. If you're still full, perhaps just grab dessert. You could stop by Garrett Popcorn for a bag of the famous Chicago mix (caramel and cheddar popcorn) to snack on. Back at the hotel, wind down and relax – you've had a full day of sightseeing.
Day 3: Art Institute & Grant Park Relaxation
Morning
Spend the morning at the Art Institute of Chicago, one of the world's great art museums. Located at Michigan Avenue and Adams Street (right next to Millennium Park), the Art Institute houses an extraordinary collection spanning 5,000 years. Snap a photo with the famous bronze lions out front, then explore masterpieces inside – from Impressionist paintings to modern art. Don't miss American classics like Hopper's "Nighthawks" or Grant Wood's "American Gothic", and be sure to walk through the stunning Impressionist galleries (Monet, Van Gogh, and more). The museum is large, so focus on a few areas of interest to avoid fatigue. (If museum-going isn't everyone's cup of tea, rest assured there are plenty of benches and even a lovely outdoor McCormick Courtyard to take a break.) When you need a lunch break, the museum has a casual café, or step outside to The Gage (a popular gastropub across the street) for upscale pub fare. Take your time – this is your one big activity today.
Afternoon
After an art-filled morning, it's time to relax outdoors. Walk a few blocks through Grant Park to Buckingham Fountain, the huge rococo-style fountain that is Grant Park's centerpiece. Fun fact: it was inspired by a fountain at France's Palace of Versailles but is double the size, making it one of the largest fountains in the world. If you're there on the hour, you'll catch the water show – the central jet shoots water 150 feet in the air! In the summer (May–October), the fountain also performs a colorful light-and-music show each hour after dusk. Find a spot on a bench or lawn and enjoy the breeze off Lake Michigan while the 17-year-old scrolls through the great photos you've taken so far. This is a perfect moment to soak up the atmosphere and rest your legs.
Evening
For dinner, you might head to the nearby South Loop neighborhood or back around Millennium Park. If you're in the mood for something different tonight, consider Lou Malnati's or Pizzeria Uno for another take on deep-dish (if you're not pizza'd out), or enjoy some Asian cuisine on Argyle Street (Vietnamese) or Chinatown – though those are a bit farther by train/Uber. Since you've had a big day, feel free to have a low-key evening. Maybe enjoy your hotel's amenities or watch a movie together. If everyone's energized, an evening walk in the Loop to see public art can be fun – you can find the Picasso sculpture in Daley Plaza or the four-story Chagall mosaic "Four Seasons" at Dearborn and Monroe. Otherwise, simply kick back and get ready for tomorrow.
Day 4: Lincoln Park Zoo & Lakefront Fun
Morning: Lincoln Park Zoo
Venture to the Lincoln Park neighborhood for a mix of nature and city vibes. Start at the Lincoln Park Zoo, one of the oldest free public zoos in the country. This 35-acre zoo is home to lions, gorillas, penguins, and more – and it's free 365 days a year. Stroll at your own pace, visiting the big cats, the primate house, or the sea lions. Don't miss the Regenstein Center for African Apes (a hit with animal lovers) and the charming Farm-in-the-Zoo. If the weather is hot, duck into the Lincoln Park Conservatory next door – this Victorian-era greenhouse is filled with tropical plants and also has free admission.
Afternoon: North Avenue Beach
After lunch, enjoy some relaxation Chicago-style: head over to North Avenue Beach, one of the city's popular sandy beaches along Lake Michigan (about a 15-minute walk or a quick bus ride from the zoo through the park). You'll be treated to a postcard-worthy view of the skyline from here. Kick off your shoes and walk on the soft sand, dip your feet in the (chilly) lake water, or rent chairs and bask in the sun. There's a boathouse with bathrooms and a snack bar if you want a cold drink or ice cream. This is a great spot for the family to just chill out – the adults can relax on the beach while your 17-year-old checks out the scene (Chicago beaches attract lots of teens and volleyball games in summer).
Evening: Old Town
Nearby Old Town is a great option to spend the evening. It's a historic neighborhood just west of Lincoln Park (you can Uber or take a quick bus). Stroll down Wells Street, which is lined with unique boutiques, eateries, and the famous Second City comedy theater. If you're interested in Chicago's comedy scene, Second City has evening improv shows (family-friendly for ages 13+; your 17-year-old is welcome with you). It's the troupe that launched many SNL comedians' careers – a show here is filled with laughs and a true Chicago experience. Alternatively, keep it low-key with dinner in Old Town: there are plenty of casual choices like Twin Anchors (an old-school rib joint) or Topo Gigio (Italian trattoria), or grab a lighter bite at Old Town Pour House.
Day 5: Museum of Science & Industry and Hyde Park
Morning: Museum of Science and Industry
Take a trip to the Museum of Science and Industry (MSI) in the Hyde Park neighborhood. Plan to spend the first half of the day here – it's huge and filled with interactive exhibits that will engage both adults and teens. Housed in a massive building from the 1893 World's Fair, MSI is one of the world's great science museums. You can descend into a coal mine, walk through a captured WWII German submarine (the U-505), and watch giant Tesla coils crackle with electricity. Don't miss the Apollo 8 spacecraft or the Mirror Maze.
Afternoon: Hyde Park Exploration
After getting your fill of science and industry, take some time to explore the surrounding Hyde Park neighborhood at a relaxed pace. Walk over to the University of Chicago campus to admire the beautiful Gothic architecture and peaceful quads. Just north of MSI is the Frederick C. Robie House, a famous Frank Lloyd Wright prairie-style home. It's recognized as one of the most important buildings of the 20th century and a UNESCO World Heritage Site. You can take a guided tour if interested, or simply appreciate the design from outside.
Evening: Local Dining
As evening approaches, consider having dinner in Hyde Park to sample the local scene. A fun, casual choice is Valois Cafeteria, a no-frills eatery famous as President Obama's favorite local spot (they even have a "Barack's Favorites" menu). "See your food" is their motto – you'll slide a tray and point to the comfort foods you want as they scoop it up. Alternatively, Medici on 57th is a beloved Hyde Park restaurant/bakery known for burgers, pizza, and huge shakes – it's a student favorite and even has graffiti you can add to the basement walls.
Day 6: Navy Pier & Lakefront Leisure

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Morning: Relaxation
Take this morning slow. Sleep in a bit and enjoy a late breakfast.

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Afternoon: Navy Pier
Explore Navy Pier, ride the Centennial Wheel, and enjoy lakefront views.

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Evening: Fireworks or Dinner
Watch fireworks at Navy Pier (if available) or enjoy a special dinner downtown.

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Night: City Stroll
Take an evening walk to see Chicago's illuminated landmarks.
Around late morning or midday, make your way to Navy Pier, the 50-acre playground on the lakefront. Navy Pier is an iconic Chicago landmark – a former 1916 pier turned entertainment district – filled with parks, rides, shops, and eateries. First, take a spin on the Centennial Wheel, the enormous Ferris wheel that soars nearly 200 feet. The enclosed gondolas provide a safe, smooth ride with breathtaking 360° views of the skyline and Lake Michigan. Back on the ground, explore the pier at your leisure: you can play a round of mini-golf, ride the old-fashioned carousel or swing ride, or pop into the Chicago Children's Museum. Street performers often dot the pier, and there are plenty of benches to sit and watch the boats go by.
Day 7: Skydeck Chicago & Farewell to the Windy City
1,353
Feet High
Skydeck Chicago observation deck height
103
Floor
Location of Skydeck in Willis Tower
4.3
Feet
The Ledge glass balcony extension
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States
Visible on a clear day from Skydeck
Start your final day with a hearty breakfast at Lou Mitchell's, a classic Chicago diner that's been serving breakfast since 1923. Enjoy a leisurely meal and soak in the old-school atmosphere. Then, ride up to Skydeck Chicago in the Willis Tower, reaching the 103rd-floor observatory. At 1,353 feet high, this is the highest observation deck in the United States, offering an absolutely jaw-dropping panorama. The thrill for many is stepping out onto The Ledge – a glass-floored balcony that extends 4.3 feet out from the building facade. It's like standing on air above the city. For your final evening, plan something relaxed and reflective. Perhaps take an early evening stroll along the Chicago Riverwalk once more, or sit in Millennium Park to watch the city lights come on. Consider a special farewell dinner with panoramic views to toast the trip. After dinner, walk over to Grant Park or Lake Michigan one last time. The city skyline from Adler Planetarium's lakeshore point is stunning at night if you want a final photo. Finally, return to your hotel to pack up and relax. Congrats, you've experienced Chicago's museums, parks, architecture, food, and some much-needed relaxation in between. Safe travels home the next day, with wonderful memories of the Windy City!