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Top Things to Do in Chicago: Highlights of a Family Vacation

Updated on October 27, 2014

Dinosaurs, Monet, Great Architecture and Baseball: Chicago Has it All!

We recently spent a seven-day vacation in Chicago, the third-most populous city in the United States. Chicago had plenty to see and do for our entire four-person family, with each of us getting to choose some attraction. There was great art and architecture for Mom, baseball for Dad, science and history for our daughter and the aquarium and amusement rides for our son.

In fact, we really had to pack in a lot each day just to see the highlights of the city! We probably could have stretched

out our vacation a few more days so we weren't rushed, but as it is we did get a good overview of the many things that Chicago has to offer. Following are the highlights of the trip, which we hope can be used as guide if you are planning on going to the city in the future.

All photos are by us unless otherwise noted.

Day One

Museum of Science Chicago WWII Submarine
Museum of Science Chicago WWII Submarine

Newborn Chicks, a German U-Boat and the Science of Storms

Visiting Chicago's Museum of Science & Industry

The museum is located on the south side of Chicago and isn't near any of the subway lines, so for us to get there by public transportation we would have had to take the subway to the center of town and either switch to a regional train line or bus. From our hotel west of the city it would have been about a 2-hour trip each way. That's too long, so since it was Sunday we decided to drive down..

And just as we pulled up a car on a street directly across from the museum pulled out, so we got free parking just about as close as we could possibly hope for! Nice way to start the trip!

The museum is located in a magnificent, sprawling building that was built as an exposition hall for the 1893 fair, and the thing that impresses you about it right away is that it is huge! There is so much to see and do that we were there the entire day and didn't get everything in. The plus side is that even on a summer Sunday it never felt really crowded. If you go plan on spending the whole day.

We really enjoyed the space area, which included the Apollo 8 Command Module that was launched in December 1968 and a lunar rock that brought back from the moon during one of the early space missions. We also attended an IMAX movie (extra fee) about the growing danger of all the space junk and satellites that are filling the orbits around the planet. Pretty amazing to think about.

Another highlight was a captured German submarine from World War II (see photo). The exhibit does a great job in explaining the dangers these U-Boats created for Allied ships, and just how difficult it was to capture one. A tour inside the sub is extra, but even without going into the vessel the exhibit is worth checking out.

The genetics area may be a bit advanced for younger visitors, with its explanation of genetic engineering and the controversy over cloning, but they will enjoy the hatchery where baby chicks are born. Other highlights are a section on how storms are created and a walk-through of a complete Boeing 727.

One thing that disappointed us a bit was the visit to the working coal mine. While the exhibit clearly showed the machinery used from past and present, we didn't think it was worth the extra money.

For More Details on the Museum of Science & Industry

Highlights of the Museum of Science & Industry: A Chicago Family Day Trip
The Museum of Science & Industry on the south side of Chicago is a wonderful place to spend a day for the entire family. The largest science museum in the western hemisphere, it has more than 2,000 things to see or do spread out over 75 halls. Original...

The Most Helpful Guidebook We Used

We usually travel with three or four guidebooks, as we find that each one contains slightly different but useful information.

This book was the one we found most helpful. An added plus is that it is slender so it wasn't a bother when we carried it around.

See below for a more extensive selection of books that we used.

Day Two

Art Institute Two Sisters Renoir
Art Institute Two Sisters Renoir

Renoir, Monet and Laughing at Modern Art!

Visiting the Art Institute of Chicago

The tour books tend to say you should plan on spending three hours at the Art Institute. But we found the museum was so filled with magnificent artwork that we ended up spending the entire day there.

The institute is famous for the Impressionist and Post-Impressionist paintings in its collection, and rightfully so. There are more than 30 Renoirs, including Two Sisters (On the Terrace) from 1881 and Lunch at the Restaurant Fournaise from 1875. Shown here is a close-up of the Two Sisters painting. In that area of the museum are also a number of Monets, Manets, Cezannes and Van Goghs (including one of his self-portraits from 1887). You could spend an entire morning just examining these masterpieces,

From that area I took my son over to the modern art wing, where visitors are greeted by an immense portrait of Chairman Mao by Andy Warhol. We listened to a tour guide talk about Dali and Pollock, then wandered among the artworks. Neither of us were impressed with the modern pieces.

We escaped back to the second level, where we winded our through old Roman artifacts, including a head of Mars from the second century A.D. We studied some Byzantine pieces, mainly because my son declared the Byzantine Empire his favorite.

We then sought out Georges Seurat's ''A Sunday on La Grande Jatte,'' which the museum calls his greatest work. I can't say whether that is true, but it is a wonderful piece. The museum placed it at the end of a special exhibition on fashion

in art, and it's an appropriate choice. Well worth checking out.

Also worth seeking out is Grant Wood's ''American Gothic,'' which I suspect is one of the most parodied pieces from the 20th century. It was also one of the popular ones when we visited, judging from the crowd around it.

By this point we were slowing down, and we walked through the American Indian, Southeast Asian and Indian, and Chinese and Korean art sections fairly quickly. Some of the pieces are interesting, but I would suggest that if you only have a certain amount of time they can be skipped. We spent a bit more time on the armor (who doesn't like knights?), but barely looked at the paperweight or miniature room collection.

While you can probably hit the highlights in an hour or so, we found that we spent five hours even with skipping some sections! So my advice is to not plan anything else for the day when you visit.

For More on the Art Institute... - Visit Our In-Depth Review Here

Highlights of Chicago's Art Institute: A Family Day Trip
The Art Institute is one of the truly must- see attractions for any visitor to Chicago. World- renowned for its Impressionist, Post- Impressionist, and American paintings, the institute says it contains about 300,000 artifacts and pieces of art spanning mo...

Wrigley Field Chicago Cubs
Wrigley Field Chicago Cubs

Seeing the Cubs at Wrigley Field

A True Chicago Tradition

That night my son and I traveled to Wrigley Field in north Chicago to see the Cubs play baseball in the ''friendly confines.'' Many tourist books list this as one of the top 10 things to see and do, and it was definitely worthwhile for us.

It's a great old-style ballpark, the second-oldest in the Major Leagues. We wandered around the place and watch parts of the game from different angles. The one strike against it is that the food choices seemed very limited compared with other parks. The emphasis here is hot dogs, burgers, pizza and sausages, with soda and beer as drinks. Not much that is healthy!

Though known as a park that can produce high-scoring games, that wasn't the case the night we were there. The Cubs lost 2-0 to the Reds in a very crisp 2:20.

Day Three

Ernest Hemingway Museum Oak Park Illinois
Ernest Hemingway Museum Oak Park Illinois

Ernest Hemingway and Frank Lloyd Wright

Visiting Their Homes in Oak Park

After our late-night at the ballpark, we decided to avoid traveling to downtown Chicago today. Instead, we drove to the suburb of Oak Park, which was only 15 minutes from our hotel. Oak Park is the birthplace of Ernest Hemingway and where the architect Frank Lloyd Wright first gained prominence, and the town does a good job of promoting and explaining its two famous ''sons.''

Fortunately, it is possible to get a good appreciation of both men on the same day with the proper planning. The Hemingway birthplace isn't open on mornings except Saturday, while the Frank Lloyd Wright Home and Studio suggests calling ahead to for reservations for a tour. So we booked our Lloyd Wright tour for the end of the day, and went to the Hemingway house for the first tour at 1 p.m.

Hemingway was born in 1899 and grew up in the Queen Anne-style home of his maternal grandparents, and the tour guide, Larry, did a wonderful job in explaining the many influences that the household may have had on Hemingway when he was a child. For example, Hemingway's grandfather loved to tell stories at the dining-room table, and encouraged the children to do the same. It's easy to see where little Ernest may have gotten his inspiration to be a writer.

Down the street from the birthplace is a museum dedicated to Hemingway, with mementos from his childhood and his career. The place does a thorough job in explaining his impact on the literary world as well as the celebrity life he led.

From there we were able to walk to Lloyd Wright's studio and home.

For an In-Depth Review of Hemingway's Birthplace See This Review

Ernest Hemingway's House & Museum in Oak Park: A Chicago Family Day Trip
Ernest Hemingway was one of the most influential American writers of the 20th century, as well as one of the most famous. A winner of the Nobel Prize for literature, the writer was born and raised in the Chicago suburb of Oak Park, Illinois. Oak Park is ri...

Learn More About Hemingway's Connection to Oak Park

Fronk Lloyd Wright Home Oak Park Illinois
Fronk Lloyd Wright Home Oak Park Illinois

Frank Lloyd Wright's Studio

Where Architectural Magic Happened

Frank Lloyd Wright became famous as a leader of the Prairie School style of architecture, which was a uniquely American style that contrasted greatly with the older, European styles from the 19th century. Lloyd Wright's works focused on horizontal lines, flat roofs and hanging eaves, and his home and studio exemplified his beliefs.

While the home was built in 1889, when Lloyd Wright was only 22 years old, it feels very modern when you go inside because of the open spaces and easy flow from room to room. Having the same color trim throughout helps emphasize that flow. What a contrast to the cramped, dark Queen Anne house that Hemingway lived in a decade later a few blocks away!

Even if you aren't a fan of architecture, this was a nice home to tour for the extra touches that Lloyd Wright built into it. The second-floor children's playroom is very open, with windows very low to the floor and extending two feet out from the walls to create even more space. It's easy to imagine children sitting there looking out at the world beyond. And because Lloyd Wright didn't like attics, what would have been some attic space above the stairwell was turned into theatre seating, so adults could sit up there out of the way and watch the kids playing.

But the touch I liked most: the room has a grand piano that is almost completely hidden inside a wall next to the stairwell. The piano's front actually extends into the space above the stairs that is usually just wasted!

In 1898, Lloyd Wright built an attached studio to the home that mainly consisted of two octagonal rooms with a rectangular room in between. It's easy to imagine the architect working with his draftsmen and artists in the space, creating new homes and buildings.

While in Oak Park, we also took time to stop by the Unity Temple, one of Lloyd Wright's most famous works. The temple, built between 1905 and 1908, is made of reinforced concrete slabs and red granite and is considered by some to be the first example of modern architecture. It is definitely worth combining with the home and studio if you have the time. Many tour books list other Lloyd Wright buildings in Oak Park that you can see from the outside and some that you can tour if you are really into architecture.

For More on Frank Lloyd Wright's Home and Studio... - ..and his Unity Temple

Frank Lloyd Wright's Home & Studio: A Chicago Area Family Day Trip
Frank Lloyd Wright was one of the most influential American architects in the 20th century, and his impact is still felt in many of the buildings that are being built today. Born in Wisconsin, he got his start in Chicago after the famous 1871 fire that lef...

Frank Lloyd Wright's Unity Temple: A Chicago Area Family Day Trip
Unity Temple, designed by architect Frank Lloyd Wright, was built between 1905 and 1908 in Oak Park, Illinois, just outside Chicago. The temple was one of the first buildings constructed with reinforced concrete as its main material, leading many architect...

Cellular Field White Sox Chicago
Cellular Field White Sox Chicago

Heading to the South Side of Chicago...

To Watch the Tigers Vs. The White Sox!

That night my son and I traveled to the South Side to visit Chicago's other major-league baseball team. U.S. Cellular Field is home to the Chicago White Sox, and it opened in 1991 as one of the more modern parks. The park is next to a huge expressway, so there isn't a neighborly feel to it like at Wrigley. Another minus is that you can't wander through the entire park like we did at Wrigley. Instead, you basically have to enter at the level of your seats and stick there.

On the plus side, there were more food choices, including some fan favorites like funnel cakes and churrasco. And the local beer was Leinenkugel's, which is a much better brand that Wrigley's choice of Pabst's old Style!

The game against the Detroit Tigers moved very slowly, and we left in the seventh inning with the Tigers ahead. As it turned out, the White Sox tied the game and eventually won in extra innings. But It would have been a very long night if we had stayed until the end!

Day Four

Seeing the Fish at Chicago's Shedd Aquarium - Penguins, Beluga Whales and Much More!

Jellyfish Shedd Aquarium
Jellyfish Shedd Aquarium

After a day of literature and architecture, we decided the children deserved a break so we headed to the aquarium! Chicago's Shedd Aquarium says it contains more than 32,000 animals, and I believe it. It's a great aquarium with a nice layout that even on a busy day didn't seem crowded.

The main area contains a circular tank filled with Caribbean fish, southern stingrays and Bonnethead sharks. Off that area are separate wings that group the exhibits in such areas as the Great Lakes, Rivers, Oceans and Islands and Lakes. Some of the more interesting animals worth seeing are the Blue Iguana, the most-endangered iguana on Earth; the Australian lungfish; and the sea lamprey (sucking at the window). There's a touch tank that enables you to feel the felt-like skin of a lake sturgeon.

Downstairs is the wild reef exhibit, worth visiting to see the araipama, the largest freshwater fish in the world. The South American fish can grow to almost 15 feet long and weigh 400 pounds!

While at the aquarium we watched a 4-D movie about animals from the South Pole to the North Pole, highlighting the lives of such creatures as polar bears, penguins and elephants. We also attended the aquarium's water show, which featured beluga whales, dolphins and sea lions. The show was decent, about on par with what we have seen at other aquariums.

We also attended the special exhibition on jelly fish, which actually was kind of small. A bit disappointing, as we expected more. We were able to look at everything in about three hours.

For More on the Aquarium

Highlights of the Shedd Aquarium: A Chicago Family Day Trip
The John G. Shedd Aquarium, located right on Lake Michigan near downtown Chicago, is a great and convenient place to spend a day out with your family. The aquarium claims to have more than 32,500 animals spread out throughout its spaces, and even though it...

A Water Taxi on Lake Michigan

Water Taxi Chicago
Water Taxi Chicago
Navy Pier Chicago
Navy Pier Chicago

Ferris Wheel and Stained Glass

An Evening at the Navy Pier

We left the aquarium in late afternoon and while we were thinking about what to do next my wife and son spotted the water taxis that ply Lake Michigan. We decided that would be a great way to see Chicago from the water, so we bought tickets ($8 for an adult, $5 a child).

We rode the lake to the Navy Pier, enjoying some great views of Willis Tower dominating Chicago's skyline along the way.

The Navy Pier is a collection of stores, restaurants and tourist attractions that opened in 1995. We skipped the stores and restaurants, but went on the high swings and Ferris wheel. The pier also had a pretty decent miniature golf course. One very pleasant surprise was a free museum of stained glass that had some really beautiful pieces.

There was a children's museum and a fun maze, but our kids are a bit too old for them.

Rather than eat at the pier we decided to walk into the city and stroll down Michigan Avenue as it grew dark. Chicago's famous Wrigley Building and nearby Tribune Tower looked magnificent at night. We ended up eating dinner at Ronny's Original Chicago Steak House, a cafeteria style restaurant that served enormous portions at very decent prices. Highly recommended.

Day Five

Sue the Tyrannosaurus Rex, Diamonds and Much More! - Visiting Chicago's Field Museum!

Sue Dinosaur Fossil Field Museum
Sue Dinosaur Fossil Field Museum

We planned to spend all the next day at the Field Museum of Natural History, and it is good that we did! There is so much at the museum that once again you shouldn't plan any other adventures on the day you visit.

The main thing we wanted to see was Sue, the most-complete and best-preserved Tyrannosaurus Rex fossil ever found. And it was easy to spot in the entrance hall. The head is upstairs in a separate exhibit on the fossil because the skull was too heavy for the skeleton to support it. And no wonder -- the skull is 600 pounds!

On the same level as the head is an exhibit called ''Evolving Planet,'' which takes a visitor through the history of the Earth's animals from bacteria to today with an explanation of the six mass extinctions that have occurred. There is a neat video display of what life might have been like in the Cambrian period, but the main attraction to this area are the fossils. There are many spanning the entire period, and the room with the major dinosaurs can take up a large amount of time. Definitely plan on spending a good hour learning about the various animals that once existed.

Other highlights to the museum included the basement's Underground Adventure, where you pretend to be only 1/100th your normal size and walk through an underground tunnel so you can see the creatures that exist beneath our feet at their ''normal'' size. I had never heard of prairie crayfish until I visited here.

The Egyptian area had some pretty cool mummies, and the younger half of Goldenrulecomics really liked the exhibit on Africa, its peoples and cultures. Less interesting were the dioramas of stuffed animals around the world and the many cases displaying many plants around the world.

One other area that I would recommend is the one on Tibet, a remote area of the world that has an amazing culture.

Day Six

Adler Planetarium Chicago
Adler Planetarium Chicago

Looking Up at The Stars...

Then Looking Down on Chicago!

We returned to Chicago's Museum Campus the next day to visit its third offering, the Adler Planetarium & Astronomy Museum. The planetarium does a nice job with several exhibits, including one highlighting the various planets of our solar system and one of the astronomy instruments used throughout the ages.

One exhibit is called ''Shoot for the Moon,'' and it tells the story of the U.S. journeys into space through the life story of astronaut Jim Lovell. Included is the Gemini XII spacecraft that carried Lovell and ''Buzz'' Aldrin into space in 1966, as well as a moon sample.

We watched an IMAX movie about the universe and the many undiscovered worlds that may exist beyond our Solar System. One thing that you need to do is make time to visit the Atwood Sphere, a 1913 planetarium that is only 17 feet in diameter. You are enclosed in the ball in the dark, and its shell has holes where the various stars above Chicago are. As the sphere rotates around you, you see the Chicago night sky all year round. A bit hokey but well worth doing.

After the aquarium, we traveled to Willis Tower. Formerly called the Sears Tower, the building is the second-tallest in North America (now that New York's new One World Center has opened) and was the world's tallest for 25 years. We were fortunate to have passes that enabled us to skip the two-hour wait to travel up to the 103-floor Skydeck.

From the Skydeck, you get a view in all four directions that is marvelous. One a clear day you can see Wisconsin, Indiana and Michigan from its windows. On this day the late-afternoon haze prevented that, though Indiana may have been visible. Still it was very cool to look down from every direction at the city.

Along the inner walls of the Skydeck are murals about Chicago's history, famous residents and notable feats including its contributions to movies and music. Well worth taking time to read all of them.

But the main attraction has to be the Ledge, which consists of glass boxes that extend 4.3 feet away from the building so a visitor is standing 1,353 feet above the city with nothing but a block of glass below! There's a steady line of people waiting to get their photos taken on the Ledge, which is understandable because it is cool!

A View From the SkyDeck

This is a short video we shot from the SkyDeck of Willis Tower, the former Sears Tower, in Chicago

For More Information on the Skydeck

Visiting the Skydeck At the Willis Tower: A Chicago Family Day trip
I first visited the Skydeck back in the mid- 1980s when I was a student in Chicago and the building was the Sears Tower. At that time, it was the tallest building in the world at 1,451 feet high. Today, it is only the eighth- tallest structure in the world...

Day Seven

Robie House Chicago Illinois
Robie House Chicago Illinois

Egyptian Mummies, Modern Art and More Frank Lloyd Wright!

A Visit to the University of Chicago Campus

We decided to spend our last day in the city at the University of Chicago on the south side, with its two museums, classic buildings and historic atomic site. And right next to campus is Frank Lloyd Wright's Robie House, one of his best-known examples of Prairie School buildings.

We started at the Oriental Institute Museum, which has artifacts from ancient Egypt, Iran, Iraq, Israel, Nubia and other areas from before 650 A.D. We were amazed at how much was stuffed within such a small building. We had planned on spending about an hour but could have taken another 30 minutes or so if we wanted to.

Highlights included a colossal bull's head from Iran dated 486 to 424 B.C., a six-ton statue of King Tut and a small fragment of the Dead Sea Scrolls. One warning: this is an old-style museum without any interactive computer displays to keep children occupied! But our kids enjoyed looking at the mummies and walking through the exhibits anyway.

From there we did the tour of the Robie House, which started with an 8.5 minute video on the construction of the building and how it escaped destruction several times over the years. The house had the feel of a museum more than a place you'd want to live in, though our guide did say one family used to have their boys run laps around the ground floor, which consists of a living room and dining room divided by a center fireplace.

Having already toured Lloyd Wright's own home, we knew many of the architectural touches that he was famous for but it was interesting to see it in another building.

After a late lunch, we walked over to the university's Smart Museum of Art. The museum contains Asian, European, modern and contemporary art and feels more like an art gallery in that it is less comprehensive than the Art Institute, for instance. We went because we wanted to see the Robie House's dining table and chairs on display, but we also enjoyed seeing a nice Rodin sculpture and a series of photographs of the Grand Canyon from 1872 by William Bell.

We walked past the exact location where the Manhattan Project team devised the nuclear reactor that produced the first self-sustaining controlled nuclear reaction in history in 1942. We wanted to visit the Rockefeller Memorial Chapel but we weren't able to go in because a wedding was being conducted, so we headed back to the hotel to pack. Our Chicago adventure was done!

Own the Robie House in Lego!

Book Your Hotel Room Today

We used Hotels.com find the place we stayed at in Chicago, and to book our other recent vacations. We haven't had a problem yet. You do have to spend a bit of time reading the reviews to make sure the hotel you select is exactly what you want, of course. Sometimes a good price just means that the hotel has had a lot of poor reviews and has dropped what it charges to attract customers!

One other bit of good news is that you get a free night's stay after booking 10 nights. The freebie has to be on a subsequent trip, but it has helped us save money. Check out Hotels.com today:

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For more about who we are and what we write about please see here:

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I hope you enjoyed reading this review as much as we enjoyed our travels and writing it. Now it's your turn!

Thanks for visiting!

Now It's Your Turn!

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    • Wednesday-Elf profile image

      Wednesday-Elf 3 years ago from Savannah, Georgia

      What a fun review of sights to see in Chicago. I've visited in the outskirts of Chicago and/or driven by several times, but have never actually been to downtown Chicago (yet). My dream is to attend a baseball game at Wrigley Field to watch one of my favorite teams, the Chicago Cubs. Glad you got to go.

    • RobertConnorIII profile image

      Robert Connor 3 years ago from Michigan

      Like to visit the skydeck!

    • goldenrulecomics profile image
      Author

      goldenrulecomics 3 years ago

      @kimberlyschimmel: That is one thing we didn't get to do. Next time!

    • Lady Lorelei profile image

      Lorelei Cohen 3 years ago from Canada

      It is nice to see the good of Chicago highlighted. Usually you hear so much negative so it is very nice to see the opposite side of this great city.

    • ThreeQuarters2Day profile image

      Dawn Romine 3 years ago from Nebraska

      Great review of things to do in Chicago, my son just moved there for college, so I'm creating a checklist of what to see in the next four years or so.

    • Brite-Ideas profile image

      Barbara Tremblay Cipak 3 years ago from Toronto, Canada

      what a beautiful city - I've never been there, but would love to see it - a lovely holiday

    • ecogranny profile image

      Kathryn Grace 3 years ago from San Francisco

      I have mostly only passed through Chicago and never got to spend much time there. You make it look like a lot of fun with plenty to see and do. I especially enjoyed meeting Sue, the Tyrannosaurus Rex. Thank you for the virtual tour!

    • kimberlyschimmel profile image

      Kimberly Schimmel, MLS 3 years ago from Greensboro, NC

      Eating Chicago-style pizza is a must for every Chicago visit. Giordano's is the best.

    • sharonbellis profile image

      Sharon Bellissimo 3 years ago from Toronto, Ontario, Canada

      I have never been to Chicago but I would love to go! Pinned for future reference.

    • profile image

      TanoCalvenoa 3 years ago

      I was in Chicago twice ever, very briefly, only at the O'Hare airport.

    • aesta1 profile image

      Mary Norton 3 years ago from Ontario, Canada

      The Frank Lloyd Wright and the Museum of Modern Art are my two top places to go in Chicago. Looks like you had a wonderful trip.

    • RhondaAlbom profile image

      Rhonda Albom 3 years ago from New Zealand

      I grew up in Chicago and went back a few years ago. It changed a lot, but most of these things I remember from my childhood. Great list. You really captured the highlights.

    • CaztyBon profile image

      CaztyBon 3 years ago

      I really enjoyed reading about Chicago. When I was a kid we lived in Indiana and my Mother worked in Chicago we would at times visit the City. I really enjoyed the visits. I would love to back as an adult and see the sites. Thanks for bringing back some great memories.

    • Pam Irie profile image

      Pam Irie 3 years ago from Land of Aloha

      I've never spent any real time in Chicago; thank you for the tour. I would have loved to take a tour of Frank Lloyd Wright's home.

    • Bill Armstrong profile image

      Bill Armstrong 3 years ago from Valencia, California

      Awesome Page, thanks for sharing!