Chicago Day Trip

A Perfect Day in Chicago

Chicago is the perfect Midwestern city. With plenty of luxurious shopping, amazing restaurants, and culture galore, visiting the city never gets old. Every trip we take is different and fun! This last time we visited, we truly created a perfect day in Chicago.

On this trip, I had a few teens along, so this is also an ideal itinerary for things to do in Chicago with teens.

Brunch is always a good idea

When traveling with teens, it’s smart to let them get ready at their own pace. It used to drive me crazy as I want to get up and started on the day, but I’ve learned to instead enjoy the downtime. While they are preparing for the day, I’ll work on my computer or read a book. Sometimes I even head down to the lobby for a coffee and chill out there so I don’t make them feel rushed.

As it’s probably later in the morning, brunch is the best plan for the first meal of the day. On our recent trip we were checking out the University of Chicago, so it made sense to find a tasty brunch spot in nearby Hyde Park.

Mesler Kitchen

After a little research on Yelp, we settled upon Mesler Kitchen in the Sophy Hotel. It turned out to be an EXCELLENT choice. The atmosphere is relaxed but slightly upscale (which feels very big-city brunch-like) and the food was delicious and plentiful.

We enjoyed splitting a veggie omelet and a big bowl of fresh berries. I added a peach mimosa, because, brunch. Terrific start to the day.

Brunch at Mesler

Enjoy some of the “touristy” stuff

We’ve visited Chicago many times, so we don’t do ALL the fun tourist attractions each trip, but we often squeeze in one or two.

The last time I visited Shedd Aquarium, I had brought just my son along, so it had been quite a few years since my daughter had visited. So, we decided to go. We purchased timed entry tickets online and grabbed an Uber from Hyde Park up to museum row.

Shedd Aquarium in Chicago

Although a bit pricey, Shedd Aquarium is a wonderful way to spend a few hours in Chicago. We touched stingrays, spent quite a bit of time watching the Beluga Whales, and wandered in and out of the other exhibits.

Insider tip: If you plan to visit more than one of the museums or traditional Chicago attractions, be sure to check out GoCity. I’ve found it to be a great money-saver on previous trips.

With time to kill before dinner, we headed over to Millennium Park to check out the Bean (Cloud Gate) and Crown Fountain. They are always terrific spots for photos and just enjoying a sunny day in Chicago.

Another fun stop for the afternoon was a trip to the Starbucks Reserve. With four levels of coffee options, it is a caffeine lover’s heaven. We had fun trying a cold brew flight (there really WAS a taste difference between the brewing methods) and a dark chocolate mocha.

Iced coffee flight at Starbucks Reserve in Chicago

Indulge in pasta for dinner

On a previous visit to Chicago, we had an AMAZING dinner in the Little Italy area. Sadly, that restaurant has moved so visiting it didn’t make sense with our evening plans, so we decided to try Gussie’s in the Near North Side.

Bread service at Gussie's in Chicago

With traditional Italian dishes at reasonable prices, Gussie’s was a terrific choice for a simple and satisfying meal. Although everything was delicious, the standout was definitely the bread. Served after we ordered, it came out fresh, warm, and covered with garlic. The smell alone was mouthwatering. When we broke it apart we were in for a delightful surprise. In between the slices was soft and flavorful cheese. So good!

Insider tip: Not in the mood for Italian? The Near North Side neighborhood has dozens of restaurant choices within a few blocks. You will have no problem finding a delicious place to eat. And on a warm evening, the atmosphere is fun and festive with diners sitting outside and music from various businesses flowing out to the street.

End the evening with a good laugh

Sometimes it can be hard to find evening entertainment appropriate for teens. Bars and many live music spots aren’t an option, and there may not be a show everyone is interested in seeing. This is why a comedy club might be the perfect solution.

Second City is a well-known comedy club in Chicago that has helped kick-start the careers of many hilarious comedians such as Tina Fey and Bill Murray. What better way to end a perfect day in Chicago, right?

Second City Comedy Club in Chicago

Typically there are several different shows to choose from and this night was no exception. We decided to go with the Best of Second City and it was an excellent decision. Our seats were fantastic and the comedians were hilarious. This show was a mix of skits and improv and both were hilarious. I’m always amazed at how quick on their feet improv comedians are. So funny.

Note: the minimum age at Second City is 10. Most of the comedy was actually quite tame and clean, but there was a bit of language and suggestive comments. I felt it was appropriate for my older teens, however, you’ll need to make your own decision for your family if you decide to visit.

Wondering where to stay in Chicago? I prefer to stay somewhere downtown and use Uber or Lyft to get around (or walking depending upon where we are going). I find it easier than driving. We typically stay at Hotel Blake on Dearborn. It’s a decent location and with a timeshare that we own, we can get a killer deal. An easy way to find a great deal is to click on the map above or use – I’ve often seen great deals on downtown rooms, including Hotel Blake on this site.

I love that every time we visit Chicago it’s a completely different trip! I don’t think I’ll ever run out of things to do and enjoy in the city. If you’ve visited, I’d love to hear about some of your favorites in the comments, so please share!

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Do you love Chicago? If so, here is the perfect day to enjoy as a couple or with a few teens along. Chicago is a terrific city for weekend getaways, day trips and more! #daytrips #MidwestTravel #getaways
Do you love Chicago? If so, here is the perfect day to enjoy as a couple or with a few teens along. Chicago is a terrific city for weekend getaways, day trips and more! #daytrips #MidwestTravel #getaways

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    1. This trip I took my daughter and a friend, but I’ve taken just my son too and he also loves the city – there is something for every kid!

  1. Hi, Pam! I loved your post. I’ve never been to Chicago, but I am going to save your post for whenever I get to visit! I thought your insider tips were awesome and your pictures and videos made the post come alive as well.

  2. Chicago really is a wonderful city, especially with teens. We had an eight-hour layover there on a recent trip and passed the day with brunch and a visit to the Bean, plus a round of mini-golf at Millennium Park. Sadly, we didn’t have time for pasta in Little Italy. We had to settle for poke and a train ride back to O’Hare but I’m sure we’ll go back soon to try some of your suggestions.

  3. Thank you for sharing this. I hope to visit Chicago this year and your post is very helpful, especially since it has been over 10 years (maybe 20) since I was last there. It was before Berghoff closed down. Berghoff beer became one of my husband’s very, very favorite. I hope to combine some of your recommendations with some of the things I saw and did when I was last there.

  4. We loved our adult trip to Chicago. At some point, we definitely want to explore a little more with the kids!

  5. Thanks for sharing some fun things to do in Chicago. I look forward to doing some of these things next time I visit.

  6. Great tips! The last time we were in Chicago my kids were little. Now that they’re teens, we will have to go back and try f=some of your suggestions!

  7. Chicago is an amazing city! It’s been awhile since we have visited, your pictures have us planning a trip!

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