10 Top Places to Visit in Chicago (solo travel Chicago for women over 50)

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For the woman traveling by herself to Chicago, there are specific sites that you must tick off your travel to-see list.  I mean, there’s is no way you can tell folks you’ve been to Chicago and yet not visited these top 10 places!

No way!

If this is your first visit to Chicago, you will want to get these crucial sites out of the way.  Give yourself a good week to conquer these fantastic attractions.


So that your next visits (and you will want to visit Chicago again and again), you’ll be free to dig a little deeper into what Chicago is all about.

But for now, let’s get down to business.  In this article, I will discuss the 10 top places to visit in Chicago for the woman traveling on her own.

Are you looking for a place to stay while visiting Chicago?  I recommend staying at an Airbnb in downtown Chicago.  Click here to begin your hunt.

Top 10 Places to Visit in Chicago

1.  Willis Tower (233 South Wacker Drive)

I still remember my first time visiting the Sears Tower (that’s what it was called back then).  I remember my ears popping as my then sister-in-law, and I took the elevator to the Skydeck (103rd floor).  It was a rainy day but clear enough for me to see the spectacular views of the city (and Wisconsin, Michigan, and Indiana).  This was my first time in a building so tall.  It was a little breath-taking being up that high (and kind-of scary).

A lot has changed since my first visit.  It’s no longer the world’s tallest building.  And it is no longer called the Sears Tower.  It is now the Willis Tower.  (It will always be affectionately known to most Chicagoans as its former name).

The LEDGE, a series of windows that extend out from the building, was added to the Skydeck as an attraction.

The addition of the LEDGE was a game changer!

The Willis Tower went from a cute little skyscraper (tongue-in-cheek) to a majorly hot not-to-be-missed place to visit should you find yourself in Chicago.

Buy your ticket online, so you don’t have to stand in line for a ticket later.  To check out prices for the Skydeck and LEDGE, click here to be taken to Viator.com.


Know before you go:

  • to beat the crowd, go early – like when it first opens
  • before you get to the Skydeck, you must sit through a video. It could take 2-3 hours, depending on the crowds, to finally get up to the Skydeck.  So again, go early before it gets crowded.
  • there’s a $75 fast pass that you can purchase to by-pass the long lines. However, if you go early you shouldn’t need the fast pass
  • once you get to the Skydeck, visibility could be crappy – you might not see much… keep that in mind.
  • there’s only one bathroom and nowhere to sit to rest your butt once you get to Skydeck.
  • wear comfortable shoes because you will be standing just about the whole time.
  • don’t try to do both the Willis Tower and the Hancock Building on the same day – trust me, it’s too exhausting.


2.  Millennium Park (201 East Randolph Street)


Millennium Park is a hot-bed of activity – no matter what time of year you happen to visit.  It is almost like a series of town squares jammed together.  Each area has a unique focal point or gathering spot.  It’s hard to believe that it all part of one park (it’s freakin’ huge).


A hundred things could be going on at once!  A band jamming at a music festival, folding chairs set up for movies in the park, folks cooling off in Crowne Fountain, lovers strolling through Lurie Garden, a runner stretching before jogging – it’s exhilarating to watch.


Know before you go:


3.  Navy Pier (600 East Grand Avenue)


Navy Pier is a pier along Lake Michigan that includes parks, gardens, a theater, entertainment center (IMAX), restaurants, retail shops, and a huge-ass Ferris wheel. It is the most-visited attraction in the Midwest and something you want to check out at least once in this lifetime.

It’s a bit touristy, but some cultural things are happening at Navy Pier that a woman over 50 might find interesting:

  • Chicago Shakespeare Theater
  • Live music series featuring jazz, classical and world music
  • Global Connections – free events featuring music, dance, and art from different cultures

Know before you go:

  • to check out what’s going on at Navy Pier,  click here or go to navypier.org.
  • there are plenty of restaurants to indulge your palate.  Prices run a bit high and the city tacks on an extra amusement tax
  • retail shops are pricey too (and have that pesty amusement tax added to all transactions)


4. 875 North Michigan Avenue (use to be the Hancock Building)

There’s another tall building that isn’t quite as famous as Willis Tower but worth seeing.  It is the 4th largest building in Chicago, and it was called the John Hancock Building until 2018.  It is now called the 875 North Michigan Building, which is a mouth-full to pronounce.

Just like the Willis Tower, the 875 N Michigan Building has an observation deck too.  It is called 360 Chicago and is located on the 94th floor. The 360 Chicago observation deck has an attraction called the TILT.

The TILT is a series of floor to ceiling windows that tilt out from the 875 Building to a frightening 30 degrees.

But what I love about the observation deck at the 875 building is you can sit on one of their wooden bleachers and gaze out on one of the most beautiful views of Chicago.

Know before you go:

  • general admission to the observation deck is around $22. It is about $8 extra for admission to TILT.  You can get a combo ticket that includes entry to the observation deck and TILT for $30.  For more information, click here to be taken to Viator.com
  • The wait times aren’t as bad as Willis Tower, but it can get busy here as well.  Pre-purchase your ticket so don’t have to stand in one line to purchase tickets then another line for the observation deck.  Once at the top, there might be another wait for TILT.
  • once you get to the observation deck, you have access to free Wi-Fi, and there’s seating.  There’s also a bar should you want an adult beverage to go with the view (smile).

5.  The Museum Campus

The Museum Campus is a 57-acre park is where the Adler Planetarium, Shedd Aquarium, the Field Museum of Natural History, and Soldier’s Field are located.  Each museum is worthy of exploring.  However, if you only have the time and energy for one museum during your visit to Chicago, I suggest checking out the Field Museum.  Here’s a breakdown of each museum:

  • Field Museum – the most famous of the three museums.  It has the largest collections of historical, biological, natural, and anthropologic artifacts.  Sue, the T-Rex dinosaur exhibit is housed here. To research or purchase tickets to the Field Museum, click here to be taken to Viator.com or click here to be taken to the Field Museum website to purchase tickets.
  • Shedd Aquarium – is one of the largest indoor aquariums and the first to include both saltwater and freshwater exhibits.  It is home to over 1500 species that include beluga whales, birds, fish, and turtles.  To purchase tickets, you can go to the Shedd Aquarium’s website by clicking here.
  • Adler Planetarium – is a museum dedicated to educating the public about the planets and space science.  It has the largest aperture telescopes in the Chicagoland area.  To purchase a ticket, click here to be taken to their website.

Know before you go:

  • You will still have to stand in line for tickets at the Shedd Aquarium and Adler Planetarium if you purchase tickets online through a 3rd party vendor.  I don’t believe that is the case if you purchase tickets online through their website.
  • If you’re looking to save money on some of the attractions mentioned in this article, I recommend purchasing the Chicago CityPASS.  The cost is $108 and includes admission to all three museums (Adler, Shedd, and Field), the Willis Tower Skydeck, and the 360 Chicago observation deck at the 875 building. For more information, click here.
  • Or you could go with the Go Chicago Card, either the all-inclusive day passes, or the 3, 4, 5 attractions Explorer passes.  For more information on the Go Card, click here.  Only the all-inclusive includes entry into Shedd Aquarium.  The Explorer passes do not include entry into Shedd Aquarium.
  • And please remember that you will most likely have to stand in the ticket line at Shedd and Adler even if you pre-purchase tickets.

6.  Buckingham Fountain

The Buckingham Fountain is one of the largest fountains in the world!  It is located in Grant Park, which is adjacent (south of) to Millennium Park.  The fountain produces a significant water show for 20 minutes every hour.  At night the Buckingham Fountain lights up, making for a beautiful Kodak moment with Lake Michigan in the background to the east and Chicago skyline wrapping around north to west.

Know before you go:

  • it’s free! The fountain cuts on at 8 AM; the water shows begin at 9 AM
  • the fountain shuts down at 11 PM every night and during the fall/winter season from mid-October to the beginning of May.


7.  Art Institute of Chicago

Located between Millennium Park and Grant Park is the iconic Art Institute of Chicago. No first-time visit to Chicago is complete until you have taken a day to explore this museum.  The Art Institute of Chicago exhibits stretches across centuries and genres.

Even if you’re not into art, you will find something fascinating that will catch your eye and capture your imagination.  It is one of my favorite museums.  It never gets boring exploring the Art Insitute because the exhibits are always changing.

Oh, and you must take a selfie with the Lion statues that stand guard outside the Art Institute of Chicago.

Know before you go:

  • go to ARTIC’s website to check out which exhibits will be showing during your visit.  Some special exhibits cost extra to attend.  Click here to be taken to artic.edu.

8.  Chicago Riverwalk

Having been stationed at Fort Sam Houston in San Antonio, TX, in the 1980s and checked out their riverwalk, I was excited when Chicago finally open up the Chicago Riverwalk; sometime in the early 2000s.  It has been modified and expanded several times since then.  It is now a 1.25-mile path full of little surprises such as a marina, a lakefront theater, restaurants, seating areas, a museum, and so much more.

If you continue along the path, it will eventually lead you to Navy Pier – which is a cool walk to do.  You pass a tiki bar, kayak rentals, and a winery along the way.

Know before you go:

  • some of the activities along the riverwalk such as the tiki bar, kayak rental are opened seasonally.  For more information on the Chicago Riverwalk, click here.


9. Chicago Water Tower 

The ornate Chicago Water Tower was built in 1869 to hide an ugly standpipe.  The standpipe was used to pump Lake Michigan water to the residents of the city.

It was one of few buildings left standing after the Chicago fire of 1871.

Today, it is the home to the City Gallery.  The City Gallery showcases works from local photographers and artists.

If you’re an architectural geek, you will love checking out the Chicago Water Tower. And why not also check out the City Gallery, as well.

Know before you go:

  • It’s free!  For more information on the City Gallery at the Historic Chicago Water Tower, click here.

10.  Museum of Science and Industry

In 1933 a building that was the Palace of Fine Arts for the 1893 Columbian Exposition became the Museum of Science and Industry It is located at 5700 S Lake Shore Drive, and not to be missed on your visit to Chicago. It is home to the largest science museum in the western hemisphere. What’s great about this museum is there’s something of interest for people of all ages.

Many of the exhibits are hands-on with the intention of sparking scientific creativity within.  Exhibits range from subjects such as energy, chemistry, design, transportation, environmental science, and so much more!

Know before you go:

  • MSI is so huge and contains so many exhibits that you should schedule a whole day for visiting all 400,000 square feet of this museum. Don’t rush and take plenty of breaks.  What’s so great about MIS is that a lot of exhibits require sitting….thank God!  My favorites are the exhibits in the Transportation Gallery.
  • For more information on tickets, exhibits, and other stuff, click here.


In this article, I discussed the top 10 places to visit in Chicago.  These top 10 sites are some of Chicago’s most popular attractions.  If this is your first visit to Chicago, you will want to get these important sites out of the way.  Give yourself a good week to conquer these amazing attractions.

Conde Nast Traveler’s readers named Chicago the number one “Best Big City.”  And there is a reason for that distinction.  Chicago has plenty of great things to see and do for the woman over 50 looking for a top-notch destination.


Are you interested in learning more about Chicago?  Check out what I’ve been writing about Chicago!

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