Chicago Attractions: Top Sights, Free Picks and a Hawaii Flight

The best Chicago attractions fall into four groups: skyline views, world-class museums, free lakefront and park time, and family stops on the Museum Campus. If you love looking down on a city from the sky, Chicago is one of the best places in the country to do it. When your travels bring you to Hawaii, the same thrill is waiting at Flight of Aloha, our Native Hawaiian-owned flying theater in Kailua-Kona and at Whalers Village in Kaanapali, Maui.

This guide is for first-time visitors, families and anyone planning a few days downtown. It gives the real prices and hours we could verify, the order that saves you the most time, and a way to take your love of big views on to the islands.

Flight of Aloha

Take the Aerial View to Hawaii

When your travels bring you to Kona or Maui, experience Hawaiian cultural storytelling through immersive flight films, motion, scents, and wind.

Visit

TL;DR

Start downtown: Millennium Park, the Art Institute and the Riverwalk fit in one walkable day.
Pick one skyline deck, book timed entry online, and go at opening or late in the day to dodge lines.
Much of Chicago is free: the lakefront, Millennium Park, Lincoln Park Zoo and the Cultural Center.
Plan 3 to 4 days for the city itself and 5 to 7 if you want neighborhoods and Hyde Park.
Heading to Kona or Maui next? Our flying theater gives you the aerial view indoors, in air conditioning, for $29.99 to $34.99.

The downtown icons worth your first day

Downtown Chicago, known as the Loop, packs the best-known sights into a small area you can cover on foot or by train. These are the ones that earn their reputation.

Millennium Park

This is the city’s front yard. Millennium Park is open daily from 6 a.m. to 11 p.m. and includes Cloud Gate (everyone calls it “the Bean”), Crown Fountain, Lurie Garden, the Jay Pritzker Pavilion and the Great Lawn. A bridge, the Nichols Bridgeway, leads straight into the Art Institute. Entry is free, so it is the natural place to begin.

The Art Institute of Chicago

At 111 S. Michigan Ave., the Art Institute is one of the country’s great art museums, with a major Impressionist collection. Adult admission is $32, with $26 for seniors, students and teens 14 to 17, and children under 14 are free. It is open Monday, Wednesday and Friday through Sunday from 11 to 5, Thursday from 11 to 8, and closed Tuesdays. Chicago and Illinois residents pay less, and free admission programs cover children under 14, Chicago teens under 18 and some other groups.

The Chicago Cultural Center

At 78 E. Washington Street, this building hosts hundreds of free programs a year. Its two stained-glass domes can be seen on complimentary guided tours. It is a good rainy-day stop and a good place to rest your feet mid-afternoon. National Geographic notes that its Tiffany dome is the largest in the world.

The architecture boat tour

Chicago is an architecture city, and the river is the best classroom. The tour departs from 400 N. Michigan Avenue. The 90-minute river cruise passes more than 50 notable buildings with certified guides, and the same guide notes it was named the top boat tour in North America in USA Today’s Readers’ Choice Awards. If you only do one guided activity, make it this one.

Skyline views: choosing your deck

Two observation decks dominate the skyline, and most visitors only need one.

Skydeck at Willis Tower sits at 233 S. Wacker Drive. General admission starts at $32 for adults and $24 for youth ages 3 to 11, and children under 3 are free. It includes the elevator ride and The Ledge, glass balconies 1,353 feet above the street. Expedited entry starts at $55. Timed entry is required, so book online first. Summer weekends can bring waits of 45 to 90 minutes even with a timed ticket.

360 CHICAGO is in the John Hancock building, on the 94th floor. It needs no timed entry, though sunset in summer, roughly 7 to 8 p.m., is its busiest window.

Two tips that apply to both:

Go right at opening, or book the last slot of the day, for the shortest lines.
Check the venue’s website that morning in winter or storm season, because both decks close for lightning or high-wind advisories.

If you plan to see several paid attractions, a bundle can be worth pricing out. The Skydeck’s own page lists a Chicago CityPASS at $144 for adults and $114 for youth, which includes the Skydeck, the Shedd and a choice of three more attractions over nine days. Do the math against the places you actually want to visit.

Museums and the lakefront

Chicago has more than 60 museums, so you have to choose. Here is a short list by interest.

Interest	Where to go	Why
Dinosaurs and natural history	Field Museum, Museum Campus	Home of Sue the T. rex
Marine life	Shedd Aquarium	Penguins, coral and belugas
Space	Adler Planetarium	The country’s first planetarium
Hands-on science	Museum of Science and Industry	Over 400,000 square feet of exhibits
Animals, free	Lincoln Park Zoo	Over 230 species, no admission

The 57-acre Museum Campus links the Field Museum, the Shedd Aquarium and the Adler Planetarium, so you can see all three without a car. The Museum of Science and Industry is at 5700 S. Lake Shore Drive in Hyde Park.

The lake itself is an attraction. National Geographic counts 24 beaches along Lake Michigan, from Oak Street Beach with its downtown skyline view to Montrose Beach with its bird sanctuary. Navy Pier runs 3,300 feet along the shore, with the Centennial Wheel and free concerts.

Chicago attractions for families

Families do best with one big anchor a day and something free to balance it.

Shedd Aquarium at 1200 S. DuSable Lake Shore Drive. Chicago residents pay a set $19.95 for adults and $14.95 for children, and general admission prices vary with how far ahead you book. Buy only from the aquarium or its approved partners.
Lincoln Park Zoo, free, and a natural add-on to a day in the park.
Navy Pier, where the Centennial Wheel is the kid favorite.
Museum of Science and Industry, which suits a full rainy day.

Chicago’s weather swings hard, so keep an indoor option in your back pocket for every outdoor plan. Museums, the Cultural Center and the library at 400 S. State Street (nearly a million square feet) all work when the lake wind turns cold.

Free things to do in Chicago

You can fill a day without buying a ticket:

Walk the lakefront and Riverwalk. Indie Campers’ guide lists the lakefront, Millennium Park, Lincoln Park Zoo and the Riverwalk as free.
Tour the Cultural Center’s domes and browse its free programs.
Walk the 2.7-mile elevated 606 trail, described in the city tourism guide.
Catch sunrise at Promontory Point in Hyde Park for an open view of the skyline, a pick from the same Indie Campers guide.
Check the Art Institute’s free-admission days if you live in Illinois.

Getting around and parking

The Loop is easiest by train and on foot, and the Skydeck and 360 CHICAGO are both close to CTA stations. If you drive, plan your parking before you leave, because downtown garages add up. This guide on parking close to attractions covers the general strategies that work in any busy tourist area: arrive early, reserve ahead and park a little farther out when the center is full.

How many days do you need?

Plan on 3 to 4 days to cover the city itself. Indie Campers recommends 5 to 7 days for a fuller trip, with May to June and September to October as the best months, and budgets of $100 to $180 per person per day for transit, meals and activities. A simple split:

Day one: Millennium Park, the Art Institute, the architecture boat tour.
Day two: Museum Campus, then a skyline deck near sunset.
Day three: Lincoln Park, the zoo and the 606 trail.
Day four and beyond: Hyde Park and the Museum of Science and Industry, then neighborhoods.

Perspective

We built Flight of Aloha for people who love the moment a city, a coastline or a whole island opens up beneath them. Chicago’s decks do that with glass and height. We do it with 8K film, motion, wind and scent, so you feel like you are flying over Hawaii.

Our theaters are indoors and air-conditioned, which makes them an easy answer for a rainy day in Kona or Maui, or for a break from the heat and vog. Our flights suit all ages and abilities, so grandparents and small kids can share the same seat row.

We are Native Hawaiian-owned, and our films carry the stories and places of the islands, like Naupaka, Lahaina, Whale Song and Europe Merrie Monarch. Families who plan their days around the best views will find that a flight with us is aerial sightseeing made accessible.

Ola

Take the sky-high view to Hawaii

If Chicago is on your list and Hawaii is too, here is how we fit in. Flight of Aloha is a flying theater in Kailua-Kona on the Big Island and at Whalers Village in Kaanapali, Maui. Our rides are an alternative to a helicopter tour, with aerial views and no motion sickness. In Kona we are within walking distance of Kailua Pier and the tender dock, so cruise visitors can fit a flight into a quick shore stop.

Single flights, such as Naupaka, Lahaina and Europe, cost $29.99 to $34.99. The Double Feature Flying Ride is $49.99 to $59.99, and the VIP Package is $69.99 to $79.99. Locals who come often can look at the Annual Pass at $200 per year. Traveling with kids? Our family attractions checklist helps you plan your day. Book online to secure your seat.

FAQ

What are the top attractions in Chicago?

Millennium Park with Cloud Gate, the Art Institute, the architecture boat tour, a skyline deck, Navy Pier and the Museum Campus are the most visited. Most can be reached from downtown on foot or by train. Choose one or two paid attractions a day and fill the rest with free stops.

What can you do in downtown Chicago for free?

Walk Millennium Park, the Riverwalk and the lakefront, and tour the Cultural Center’s stained-glass domes. Lincoln Park Zoo is also free and a short ride north. These cover a full day at no cost.

Which Chicago attractions are best for families?

The Shedd Aquarium, Lincoln Park Zoo, Navy Pier and the Museum of Science and Industry are the usual picks. Pair one ticketed stop with one free stop each day to keep kids happy and costs down.

Is there something like Chicago’s skyline decks in Hawaii?

Our flying theater gives you an aerial view of the islands from a seat indoors. It is at Kailua-Kona and Whalers Village, Kaanapali, and tickets start at $29.99 for a single flight. You can book online ahead of your visit.