Chicago Sightseeing – Best Attractions, Tours and Places to Eat

This time we put together some ideas and trip planning tips for Chicago sightseeing. The windy city has many great attractions, some are obvious while others may not. These are my tips for someone who has never been to Chicago before and wants to experience this fantastic city for the first time.

Chicago sightseeing

By foot, bus, bike, or boat .... find the best rated Sightseeing Tours in Chicago right here on TripAdvisor!

Chicago sightseeing by hop-on hop-off bus.  The Chicago sightseeing bus (Big Bus) provides great views of the city. The tour guides are well versed with the architecture, history, and pop culture within the city so you learn a lot while enjoying the views. Take the tour on your first day and then build your sightseeing itinerary from there.

Start your walking trip in Chicago with a tour down Chicago Riverwalk. If the weather is nice, there’s no better way to be introduced and learn about the history and architecture of the buildings. The walk along the Riverwalk from Lake Street to Lake Michigan is about 1.25 miles. Although the Riverbank is not fully completed you get great views of the confluence of the north and south branches and great views of Wolf Point. Just walk along the river and take in the grandeur of the skyscrapers, you get many excellent photo opportunities here. Address: 100 E. Wacker Drive Chicago, IL 60601.

Follow us for the the ultimate Chicago sightseeing experience up in the clouds.

chicago 360 observation deck

360 Chicago Observation Deck, Hancock Building

On 360 Chicago Observation Deck, Chicago is for you! Formally called the John Hancock observatory, it can be accessed from the north end of the Magnificent Mile. Buy a one time ticket or one for a morning plus night visit. It´s wonderful to see how the skyline and the shoreline changes when looking at it from 94th floor at night! If your budget allows, skip the observation floor and head right up to the Signature room and lounge on 95th floor for a cocktail, fancy lunch or dinner. Address: 875 N Michigan Ave 94th Floor Chicago, IL 60611-1803. Open: Sun to Sat 9:00 am – 11:00 pm. For short waiting times come early.

Why settle for a crowded Chicago sightseeing bus when you can see Chicago’s landmarks and attractions from the water?

Use the Chicago Water Taxi  for an easy and scenic means to get around, totally local style. This is a great way to see Chicago from the river or the shoreline. You can enjoy the views and water at the same time, plus get to your destination. If you just want to sit back and relax or take some awesome photos of the lake front, this is the way to go. It is well priced (all day ticket $9) and easy to access. The Chicago Water Taxi has several routes that encompass the shorelines of Lake Michigan as well as a trip down the Chicago River.  Address: 400 N. Michigan Avenue Chicago, IL 60611. Hours: Sun – Sat 6:45 am – 9:00 pm

The best historical Chicago sightseeing by boat!

Chicago’s First Lady Cruises is one of the best ways to get an historical overview of the city.  The First Lady Cruises are the official cruises of the Chicago Architectural Foundation and the staff are highly trained docents from the Foundation. Most of these are volunteers and have an amazing knowledge of the buildings you will see on the cruise. Address:112 E Upper Wacker Dr Southeast Corner of Michigan and Wacker Chicago, IL 60601. Operating hours: Mon – Wed 9:00 am – 4:00 pm, Thu – Sun 9:00 am – 5:30 pm.

Chicago things to do

Shedd Aquarium

Shedd Aquarium is one of the best aquariums in the world. Don’t leave Chicago without spending the day exploring it. You can see Nemo, sharks, seals and more, plus there are usually some shows a few times throughout the day. If you want to make this a once in a lifetime adventure add on a special event, like shark feeding for $89.95 for adults. Address: 1200 S. Lake Shore Drive Chicago, IL . 60605. Opening hours: Mon – Fri 9:00 am – 5:00 pm, Sat – Sun 9:00 am – 6:00 pm. Admission $8 for adults and $6 for kids.

More Chicago sightseeing opportunities, from museums to fountains.

Chicago things to see

Field Museum

The Field Museum is amazing and huge and all about the natural history of the Earth. There are so many different exhibitions here. And they have Sue, the world’s most intact T-Rex skeleton. If you like coffee, purchase a large from the cafe and get free refills.
Address: 1400 S Lake Shore Dr Chicago, IL 60605-2496 (close to both the Shedd Aquarium and the Adler Planetarium). Hours: Sun to Sat 9:00 am – 5:00 pm.

At the Museum of Science and Industry there are so may really cool things to see. It’s geared mostly towards kids, but there is plenty to see and do for adults too. The  building was part of the Chicago World’s Fair Exposition in the 1893. But many of the attractions charge an extra fee, like the U505 submarine, the gigantic model rail road as well as the space center. Address: 5700 S. Lake Shore Drive Chicago, IL 60637-2093. Admission is around $20/person.

Get an overview, have a look at the Chicago sightseeing map & attractions map right here.

If you like outer space  Adler Planetarium is the place for you. They have such a good program, very educational and entertaining, kids will love the star show too. 1300 S. Lake Shore Drive Chicago, IL 60605. Hours: Sun – Sat 9:30 am – 4:00 pm. Price: $12

Totally free Chicago sightseeing attractions.

Lincoln Park Zoo is great and it is FREE.  There is lots to see and explore here, you should bring a picnic lunch. Address: 2001 North Clark Street Chicago, IL 60614. Opening hours: Sun to Sat 10:00 am – 5:00 pm.
Take the chance and walk just outside the north gate and see the Lincoln Park Conservatory as well. You´ll get taste of the tropics right in Chicago. Something different is in bloom or ripening  all the time. Wonderful old Victorian structure. On weekends ask a docent for a free tour, they will add a lot to your experience. Address: 2391 N Stockton Dr At Stockton Dr. Chicago, IL 60614. Hours: Sun – Sat 9:00 am – 5:00 pm. Admission: free

sightseeing in Chicago

Buckingham Fountain

By foot, bus, bike, or boat .... find the best rated Sightseeing Tours in Chicago right here on TripAdvisor!

Make sure you don´t miss the Buckingham Fountain on your Chicago sightseeing tour. You can visit Buckingham Fountain at any point of your trip, but at dusk there’s a beautiful twenty minute water show with music and lights for you to enjoy! This is a great spot for relaxing, daydreaming and a picnic.  It is also a favorite spot for couples taking wedding photos in front of the fountain. Address: Grant Park Chicago, IL.

Fascinating Chicago sightseeing  – architecture and historical monuments.

Architecture lovers will like The Rookery in the loop! Definitely a must see if you are into Frank Lloyd Wright work. Join a tour, it allows you to go up the stairs and view it from the balcony and see the spiraling interior fire escape, you´ll also see the Burnham library where the architects had their office. Find the next upcoming tours here.
Address: 209 S. LaSalle St. Chicago, IL 60604. Hours: Mon – Fri 8:00 am – 6:00 pm Sat 8:00 am – 2:00 pm. Did you know that the “Historic Route 66 Begins Sign” is on the corner of the tiny fenced park at Adams and Wabash.

Chicago sightseeing that kids can enjoy.

Chicago sights

Navy Pier

At Navy pier you can enjoy some spectacular views of the Chicago skyline. There is also a good choice of restaurants and fast food. You can catch a nice view of the lighthouse from the end of Navy Pier in Downtown Chicago. If you come with kids visit the Chicago Children’s Museum and the iMax. Address: 600 E Grand Ave Chicago, IL 60611

Chicago sightseeing from art and movie places to ethnic neighborhoods, and shows.

Chicago must see

Millennium Park, The Bean

For art lovers a trip to Chicago wouldn’t be complete without a picture of your reflection in ‘the bean’ at Millennium Park. The plaza with Cloud Gate is fun to walk through and take pictures.  The modern architecture of the concert area and foot bridges add a special modern beauty to any walk. Address: 201 East Randolph Street Between Michigan Avenue & Columbus Avenue Chicago, IL 60601.

The Art Institute of Chicago is a must see and so much fun to explore. This fantastic art museum is open from 10.30am until 5pm, with a late night on Thursdays until 8pm. Group and self-guided tours are also available.  Address: 111 S Michigan Ave 159 East Monroe Street Chicago, IL 60603. Opening hours: Thu 10:30 am – 8:00 pm Fri – Wed 10:30 am – 5:00 pm. Admission range: $25 – $25.  Free entry every Thursday, 5pm – 8pm.

Another highly photographed landmark is the Picasso Statue. Chicago got this unique sculpture and its there for all to see. An added bonus, if you visit on a Thursday between 7 am and 3 pm from May 15 to October 30, you can grab something fresh from the farmers market. You can find everything there from fresh flowers to cheese, Amish baked goods and veggies and fresh fruit for your hotel room.
Address: 50 West Washington Blvd, Richard J. Daley Plaza Civic Center, Chicago, IL 60602

Chicago attractions

Union Station

By foot, bus, bike, or boat .... find the best rated Sightseeing Tours in Chicago right here on TripAdvisor!

Union Station is beautiful building and has been featured in many movies, including The Untouchables and Man of Steel. It is considered a “Great Public Space” with exemplary character, quality, and planning. You can either walk the space for free or get a real sense of the history and architecture by taking a one hour tour for $15 offered by the Chicago Architecture Foundation.
Address: 225 South Canal Street, Chicago, IL 60606

Enjoy Chicago sightseeing the Asian way.

Chinatown  is a great area to spend some time and it is easy to get to on public transport. The Nine Dragon Wall (a reproduction of the original wall in Beijing from 1402) is a famous landmark here, it´s located across the street from the Wentworth entrance. Take your time walking down the street and looking in the shop windows. In Chinatown you can find many things that may be difficult to find anywhere else at great prices. Chinatown Square is a great place to take your picture with the sculptures of your animal from the Chinese Zodiac. For foodies this is the opportunity to have great authentic dim sum. Address: 318 West Cermak Ave Chicago, IL 60616

A must do Chicago Sightseeing for sport fans.

Sightseeing Chicago

Wrigley Field

Sports fanatics love Wrigley Field as this is the classic of all ‘ball parks’!  There is endless options for nightlife and food in the area to pair with a game at the field! There are often concerts held here in the summer too! Address: 1060 W Addison Chicago, IL 60613-4397. There is a 75-90 minute guided tour for $25, an experience you will remember for a long time if you are a history or sports buff.

Chicago sightseeing comes in all forms, there are even beaches.

North Avenue Beach is one of the major beaches in the concrete jungle! The beach and water are really clean. There are lots of places to eat, food stands available. In summer it is always packed, and there are many activities from volleyball, stand-up paddle boarding, or jet skiing. Address: 1600 N. Lake Shore Dr Chicago, IL 60614

Chicago sightseeing locations for the shopping traveler.

chicago shopping trip

Michigan Avenue / The Magnificent Mile

Even if you don’t like shopping you can’t visit Chicago without at least taking a stroll down The Magnificent Mile.  If your favorite chain is usually difficult to find, odds are they do have an outpost right here in Chicago. You can find plenty of stores just off the Magnificent Mile on Rush Street. It runs parallel, and also has some great 5-star restaurants in case you get hungry. North Michigan Avenue Chicago, IL 60611

Water Tower Place is located on the Magnificent Mile. Especially on a cold and windy day in Chicago this is a fine and more inexpensive place to shop. It’s worth stopping by to appreciate its architecture. Address: 835 N. Michigan Avenue Chicago, IL .60611.  Open: Sun 10:00 am – 6:00 pm, Mon – Sat 10:00 am – 9:00 pm.

Chicago sightseeing for foodies, get restaurant tips and best places to eat in Chicago.

After all the sightseeing in Chicago you’ll have worked up a big appetite. Check out the best Michelin star restaurants in Chicago:

Like pizza? Than just head on over to Gino’s East for a famous Chicago-style deep dish pizza. You better show up early to avoid the dinner rush, your pizza will take about 45 minutes to prepare, you’ll be hungry by the time it arrives.
Address: 500 N. LaSalle St Chicago, IL 60654. Hours: Sun – Thu 11:00 am – 10:00 pm Fri – Sat 11:00 am – 11:00 pm. Price range: $0 – $30

If you love meat The Publican is right up your alley. Definitely a place to order pork and seafood dishes, think about pork shoulder, french toast with raspberry sauce, sausage and bacon pancakes. This is a loud, bright open space and a lovely place for a family brunch! Make a reservation (+1 312-733-9555) this place is popular with the locals. Address: 837 W Fulton Market Chicago, IL 60607-1318. Price range from $25 to $100.

Sometimes lunch in Chicago can be a bit pricey, so if you are looking for a unique fun and less pricey lunch experience try a picnic in one of the parks. Just stop in at Pastoral Artisan Cheese, Bread & Wine and pick out some bread, couple cheeses, or some artisan sandwiches and a bottle of wine and head over to Millennium Park or Cloud Gate and enjoy an afternoon outdoors. You can choose to eat in too, as they feature tables or a bar type setting. There are great food items here in any price range, so this can be as inexpensive as you like or a luxury splurge. Address: 53 E Lake St, Chicago, IL 60601-5904 (a 10 minute walk from the Art Institute of Chicago).

Russian Tea Time is the perfect place for a delightful afternoon tea break on your Chicago sightseeing tour.  The tea is was lovely and plentiful and so are the bites. Try the beef stroganoff, it will be the best you´ve ever tasted. Vodka tasting is also a must. Address: 77 E Adams St Chicago, IL 60603-6109. Hours: Sun – Thu 11:00 am – 9:00 pm, Fri – Sat 11:00 am – 11:00 pm. Price range: $20 to $30.

Or grab a dinner and a few drinks at Rock Bottom Restaurant & Brewery. The beer is delicious and portion sizes are large. Rock Bottom can get busy, but they have plenty of beers to try while you wait. Address: 1 W Grand Ave Chicago, IL 60654-4806. Open: Sun – Sat 11:00 am – 2:00 am.  Price range: $7 – $25.

Chicago sightseeing is fun during the day and entertaining at night.

Visit Second City Comedy Clubs for a night of laughing without the kids. Snacks and alcohol are always available throughout the performances. , so that being said, this one is not for those traveling with kids. The actors are amazing and the entire show is filled with laughs, excellent value for the money.
Address: 1616 N Wells St Chicago, IL 60614-6002. Shows usually start at 8 pm and 11 pm.

Thought there are no more Chicago sightseeing ideas left, think about music.

If you still have energy left after a long day exploring and doing sightseeing Chicago, head on over to Howl at the Moon and sing the night away! You can always put in your requests for songs, it’s guaranteed fun for everyone.Highly recommend if you like live music.  If you arrive early enough there isn’t any charge to get in. Address: 26 W Hubbard St Chicago, IL 60654-4606. Open: Sun 7:00 pm – 2:00 am, Mon – Fri 5:00 pm – 2:00 am and Sat 5:00 pm – 3:00 am.

I hope these tips on Chicago sightseeing make your visit as pleasurable as possible.