The Unknown Ahead

Welcome to the Windy City! Did you know the first skyscraper in the nation was built in Chicago? Built in 1884, it was only 10-stories tall, but the Home Insurance Building was an impressive structure nonetheless for the time. Chicago was also the home of the world’s tallest building from 1974 until 1998. Most Chicagoans still call it the Sears Tower, but it’s now known as the Willis Tower. You can still go up to the Skydeck at the Willis Tower and see the view from 1,353 feet in the air.

Chicago has so much to be proud of in its 187 years as a city. This isn’t a history blog, but did you know that Chicago was famous for…

• Inventing the first refrigerated rail car
• Holding the World’s Columbian Exposition of 1893 (did anyone read The Devil in the White City?)
• Using a grid layout? After the city burned down in 1871, it was rebuilt in a grid, so it’s really easy to navigate.
• Inventing the TV remote control (Zenith)
• Creating the first self-sustaining nuclear chain reaction at the University of Chicago in 1942
• Reversing the flow of an entire river!
• Starting place for Historic Route 66
• Having 28 miles of lakefront property and 24 beaches
• Inventing the brownie at the Palmer House Hilton
• And of course, the deep dish pizza

Chicago is home to many world-class museums, music venues, restaurants, and great architecture too. Ready to start exploring? As a Chicago native, it was really difficult to whittle down all that the city has to offer, but this itinerary should give you the highlights. I’m going to assume you’re not visiting in the dead of winter (please don’t), but I will include some snowy weather ideas too. Let’s start exploring!

Where to Stay

• Chicago has a lot of amazing hotels, so you really can’t go wrong. Here are my favorite places to stay in the city:
  • Chicago Athletic Association – This is a Hyatt affiliate, so use those points! The CAA is a gorgeous building with a huge lobby, amazing bar and game room, and a famous rooftop hangout called Cindy’s (Top Chef fans? Check it out!). A room with two double beds goes for about $300 per night. The CAA offers a great location in the Loop and is across the street from Millennium Park.
  • Hilton Palmer House – The lobby in this hotel will blow your mind. The location is perfect and walking distance to theaters, Millennium Park and the Art Institute. Rooms with double beds go for about $250 per night. There is a great indoor pool to tire out the kids in the evenings. The brownie was invented in this hotel, so be sure to indulge in a little dessert!
  • The Moxy – This Marriott affiliate has a really fun and quirky vibe. In the River North neighborhood, this hotel is near the Mag Mile shopping area and many restaurants and bars. The lobby offers vinyl records to play, video games, and plenty of other family oriented activities. This is a cool option for families because they offer rooms with a queen bed and a loft bed for little ones. These rooms go for around $220 per night. Did I mention that they have a late night taco place in the hotel? I might have had some midnight nachos there once…
  • Langham – If you’re looking for luxury on the river, it can be found here. It’s been voted one of the best hotels in Chicago for good reason. This is more pricey at $500ish per night, but the location is pretty unbeatable. They also have an indoor swimming pool. If you can escape the kids for a few hours, the Chuan Spa is amazing.
  • Blackstone – This hotel is part of the Marriott Autograph Collection, so another opportunity to use points! Rooms are $200+ per night depending on the view. The Blackstone is further south than the other hotels on this list, but very close to the museum campus and aquarium. You’re basically across the street from Buckingham Fountain.
  • Hotel Lincoln – This hotel is the furthest north on the list and is located in Lincoln Park near the Lincoln Park Zoo. It’s a World of Hyatt member, so another way to spend those credit card points! The J Parker is a great rooftop bar, especially during the holidays when you can see the Zoo Lights display. A room with two double beds is about $200 per night.

Can’t get into your hotel or rental until check-in time? You’ll need a place to stash your luggage while you roam Chicago! Look no further than Radical Storage! They have a lot of secure and convenient locations to drop off your bags for a few hours or the whole day. Highly recommend!

Day 1

• It’s your first day in the city, so let’s take in the views! Walk or get an Uber to the Hancock Building off of Michigan Avenue. We’re going 1,000 feet up to check out the 360 Chicago experience. Look at ticket options HERE. You can take in the views of Chicago, try the TILT, and get a mimosa at the CloudBar. The most expensive option gets you everything and a souvenir glass – about $50 per adult and nearly $40 per kid. General admission to the observation deck is $30 per adult and $20 per child. You also have the option of getting the Chicago City Pass which makes a lot of sense if you’re visiting museums too.
• After taking in the views, let’s check out the famous Mag Mile. Pop into the Starbucks Reserve and revel in several stories of coffee greatness. You can try exclusive coffee and espresso concoctions or indulge in a few coffee martinis. There’s a rooftop space here too, if the weather is nice. If you’re traveling with little girls, be sure to pop into the American Girl Place. Not only can you shop, but there’s a salon, dining, and high tea too! Keep walking south along Michigan Avenue to the river. Stop and shop along the way, of course! If you need some lunch or sweets at this point, you have a lot of options:
  • Ghirardelli Ice Cream & Chocolate Shop – Just as delicious as it sounds. They have amazing shakes.
  • The Purple Pig Restaurant – This is a top restaurant in Chicago. If you’re traveling with kids and want to experience some great restaurants, sometimes it’s easier to try them over lunch.
  • Ed Debevic’s – Classic diner food, but the waiters are rude to you on purpose. Super funny spot to take the kids for some burgers.
  • Eataly – This might be my favorite spot in all of Chicago. You can peruse the first floor for kitchen gadgets, little desserts, olive oil, wine, etc. Go upstairs, and you can enjoy several Italian restaurants, glasses of wine and a microbrew. Despite all of the wine and beer, this is a really family-friendly location for a meal or snacks. They make burrata in house…so gooooooooood.
  • Lou Malnati’s Pizza – Chicago is famous for their deep dish pizza, so give it a try. It’s a lot of cheese. Like, a lot of cheese.
• Once you hit the river, hop on a Wendella Boat Tour to see Chicago’s architecture from the water. You can opt for a 45 or 90 minute tour. To be honest, I love these architecture tours and have been on this tour at least ten times. I still love it. The guides are really funny and you’ll learn a lot about the history of Chicago. Little kids will still enjoy it because you’re on a boat and there’s lots to see. Even if the architecture part is lost on your children, it will still be a highlight of your trip.
• When you’re done with the boat ride, walk the river walk and enjoy the views and people watching. There are plenty of little cafes and ice cream shops to keep you happy. If you want to venture a few blocks south on Michigan Avenue, check out the Nutella Cafe for a little treat.
• Once you’re ready for dinner, there are a lot of choices right off of Michigan Avenue that are delicious and won’t break the bank.
  • If you didn’t do Eataly for lunch, consider it for dinner. I think it’s a must-do in Chicago.
  • RPM Seafood – Needs no explanation, just amazing seafood in a beautiful building.
  • Quartino Ristorante – Small plate Italian meant to be shared around the table. Get the meatballs for sure.
  • Looking for something a little fancier? Try out avec in River North. Mediterranean food with a twist and a great wine bar.
• Today was all about taking in the city, checking out Michigan Avenue, and having some great food. If you’re with a 21+ crowd or have a sitter, there are a lot of fun bars in this area too. Howl at the Moon is a dueling piano bar that is a lot of fun. There’s also Pops for Champagne just a few blocks away.

Day 2

• Today is a great mix of museums and lake front fun. We’re starting at the Shedd Aquarium. This is one of my favorite places in the world. I’ve been going to the Shedd since I was a toddler, and it still brings me joy to this day. The reef exhibit is gorgeous and full of sharks. The Shedd also has a dolphin show and beluga whales. Although you could spend a whole day here, we’ll just check it out as an AM activity. If you opted for a Chicago City Pass, you’ll get free entry here. If not, tickets run about $40 for adults.
• The Field Museum is literally across the street from the Shedd. You could pack another museum into the day, if that’s your vibe. You could also wait and do “Day 2” on a bad weather day. The Field has a lot of animals, dinosaur bones, DNA lab, Egyptian mummies, gems and jade, African artifacts, and much more.
• Once you’re done with the museum campus, walk north along the lake. Did you know that the entire lake front is public property in Chicago? As you walk north, you can look at Buckingham Fountain, have a hot dog from a street vendor and end up at Maggie Daley Park. If you have kids, you must visit this playground. It’s epic. Not only is the playground beautiful, but the views of the city are great too. If you want some fantastic Chicago pictures of your kids, this is the place to get ’em.
• Once you’re done playing, check out The Bean and Millennium Park. These are great open spaces for your kids to run around. Be aware that Millennium Park has some water features…so if it’s summer, the kids might get wet…
• In the summer, there are free concerts on the lawn of the Jay Pritzker Pavilion. People bring charcuterie and bottles of wine to enjoy on a picnic blanket here. You can see the line-up of events here.
• If you’re looking for some dinner in The Loop, check out these suggestions
  • Russian Tea Time – this is great winter food, but good any time of the year. I love that they have shareable sample platters so that you can taste everything. If you’re looking for my favorites though, it would be the quail or beef stroganoff. There is a full kids menu as well. My favorite thing about this restaurant though is the line-up of vodkas on the menu. If you want some good vodka shots or flights, this is your place.
  • The Gage – Diverse menu and great cocktails, The Gage is right across the street from Millennium Park. If you’re staying at the Chicago Athletic Association, it’s conveniently next door.
  • Exchequer – Just a good pub. This is bar food and pizza, but really tasty.

Day 3

• We’re going north today to check out the Lincoln Park neighborhood. Our first stop is the Lincoln Park Zoo. This zoo is totally free! Just walk on in through the main gates and start looking at the animals. The ape house is really excellent. There’s also a children’s area with a huge indoor play place. Just south of the main zoo is a petting zoo and farm area too.
• When you’re done with the zoo, walk a block north to the Peggy Notebaert Nature Museum. This little museum won’t take a ton of time, but there is a butterfly house and a lot of imagination space for little kids.
• If you’re in need of some lunch, check out Cafe Ba-Ba-Reeba! Delicious Spanish tapas with something for the whole family. Or you can eat nonsense for lunch at the zoo and save this gem for dinner.
• Since you’re in the Lincoln Park neighborhood, you should absolutely see The Blue Man Group. It’s an easy walk from the zoo. This music-meets-entertainment-meets-paint show is so much fun for the whole family. Tickets aren’t that expensive, and you get to indulge in adult drinks in the theater. That’s a win. We were in the splatter zone, and it was still a great time. Just beware that there are a few moments where they get someone from the audience to participate…just don’t make eye contact…

Day 4

• Today we’re going south to explore Hyde Park. If you’re interested in architecture, you can take a quick tour of the Robie House created by Frank Lloyd Wright in 1910. It’s only open Thursday through Monday from 10 to 2:30.
• Next, we’re spending the rest of the day at the Museum of Science & Industry. This museum is housed in one of the remaining buildings from the 1893 Columbian Exposition. There is a really interactive area that teaches kids about weather, and they can stand inside a tornado. The museum also boasts a U-505 submarine that is captivating for kids and adults alike.
• There is a growing food scene on the south side that you can’t miss. For dinner, I suggest 14 Parish for some Caribbean fare. There’s also a place called Virtue that has some delicious southern food. Get reservations in advance.
• If you didn’t use the whole day at the museum and have some time on your hands, you could also hop up to Chinatown and explore. This area would also have plenty of great dinner choices.

Day 5

• Let’s visit one of the most touristy places in Chicago – Navy Pier. Depending on your kids ages, there are a lot of options in this area. The pier itself is fun to stroll. It’s an iconic spot to take pictures, enjoy the lake, and grab some easy food. Here are some of the highlights:
  • The Ferris Wheel – Go up 200 feet in the air and get some great views. I would buy tickets in advance since it’s a popular Chicago activity.
  • Children’s Museum – This is a really fun and interactive choice for littler kids. I’d probably suggest this for kids under the age of 8.
  • Flyover in Chicago – “Fly” through Chicago’s skyline in this ride/movie adventure.
  • Shakespeare Theater – If you’re in the mood for a play, this is a really cool theater-in-the-round experience.
  • Free fireworks every Wednesday and Saturday during the summer. The display usually starts around 9:30pm.
  • Get out on the lake with a Seadog speedboat cruise. These are a lot of fun for all ages. You’ll cruise around the lake front and learn a little bit about Chicago, but then they go full throttle for some speedy fun and 360 degree spins. You will definitely get wet.
• You could easily spend the whole day on Navy Pier, but if you need an activity to fill in the gap before dinner, the Museum of Ice Cream is a 20 minute walk away. This is a major Instagram spot if you’re looking for some cool pictures of the kids.
• Check out some of the restaurants from Day 1 on the itinerary since you’re back near Michigan Avenue.

Day 6

• If you’re looking for another skyscraper experience, we’ll check out the view from Willis Tower (formerly Sears Tower). Go up to the SkyDeck and see if you dare to stand on The Ledge. This is the tallest building in Chicago, and it’s still the 3rd tallest in the Western Hemisphere. The SkyDeck is on the 103rd floor, so you’ll get quite a view on a clear morning.
• Next, you have a few choices (or do them both!):
  • The Color Factory is right next to Willis Tower. This is another Instagram type of opportunity. I haven’t been here yet personally, but people seem to enjoy it.
  • The WNDR Museum is like being in an interactive digital art space. You can spend a few hours here exploring the different rooms and exhibits.
• In this area you can find some really good food. I love the Time Out Market because it brings together really good chefs from all over the city. This place can get pretty busy, but I think it’s worth it. There are 21 different restaurants to choose from and all types of cuisines. Tables are communal, so it can also be a fun way to meet people.
• Chicago offers a lot of nightlife choices that the whole family can enjoy. Depending on the time of year and your family’s ages/interests, check out the following:
  • Broadway in Chicago – There are many amazing and gorgeous theaters in Chicago. Shows obviously change year-to-year, but there are usually family-friendly choices like Into the Woods, Wicked, Hamilton, Mamma Mia, etc.
  • Chicago Symphony and the Lyric Opera – Both organizations are right in the Loop and in lovely buildings. If you’re here during the holidays, the CSO does a great Christmas series.
  • Second City comedy in Chicago started a ton of famous careers like Tina Fey, Stephen Colbert, John Belushi, Bill Murray, John Candy, Dan Aykroyd, Steve Carell…this list goes on forever!
  • There are plenty of 21+ music venues in the city too. If you’re looking for some live jazz and blues, check out Kingston Mines or Green Mill.

Day 7

• It’s your last day in the city! Here are some final thoughts depending on the time of year:
  • The Art Institute – This is one of my favorite places in the city, but I know that art isn’t always a big hit with littler kids.
  • If it’s summer, have a beach day! Lake Michigan offers some nice sandy beaches. I’d suggest Ohio Street Beach, Oak Street Beach or North Avenue Beach.
  • Chicago has plenty of sports options! Depending on the season, you can catch a Cubs baseball game and check out Wrigley Field. We also offer the Bears, Blackhawks, and Bulls. There are plenty of choices if your family is in the mood for some athletics.
  • The Chicago Botanical Gardens is a beautiful way to spend an afternoon, but be warned that it’s actually in the suburbs quite a bit north of the city. You’ll likely need a rental car for this one. If it’s summer, Ravinia is in this neighborhood too. Ravinia is an outdoor music venue where you can enjoy a picnic on the lawn or reserve seats in the pavilion.
  • If you’re visiting during the winter months, there is a Skating Ribbon available near Millennium Park. There are also several Christmas Markets that open up in the city, but be warned that they get really crowded.
  • There are some great food tours if you want to walk and eat your way around the city. Did you watch the TV show The Bear? Yes, Chef! There’s even a tour for beef sandwiches.
  • Speaking of tours, there are also plenty of history tours including Al Capone and Chicago gangsters from the 1920s.

Tips to Getting Around in Chicago

Personal opinion, but I don’t think Chicago has a great public transit system. We do have “The L” which is the train system. These lines are color coded, but don’t always easily connect from place to place. Some of the lines close down earlier than others too, so if you’re out late at night take a look at the train schedule ahead of time. You can find a map HERE. If you want to get to Chicago from O’Hare Airport, you can get on the Blue Line to head downtown. You may want to get the Ventra App if you’re planning to take trains or buses.

If you have a car, I would strongly suggest the app SpotHero. This will show you all of your parking options and the price upfront. I use this app every time we go downtown and it saves us a ton of money.

I think the easiest way to navigate Chicago is via Uber or Lyft.

Check out all of my Chicago suggestions on this interactive Google map!