Summer Chiago Itinerary

Plan The Perfect Weekend Chicago Trip Itinerary – Top 26 Summer in Chicago Activities

Do you want to plan a weekend in Chicago trip itinerary? Awesome, we are going to plan the perfect 3-day Chicago itinerary.

Chicago is such a fun place you could easily take this weekend Chicago trip itinerary and make it adaptable to the amount of time you will be in the city. There is enough information in this post to plan a Chicago itinerary for 7 days. How does 1 week in Chicago sound? 

No matter how long you decide to spend in Chicago, we have you covered! We will help you plan a 3-day Chicago itinerary, a 5-day Chicago itinerary, or a full week in Chicago!

In this post, we are going to focus on Chicago in the summer and all the things to do in Chicago that you have to include on your weekend trip to Chicago! 

My husband grew up near Chicago, so we have been many, many times! I am excited to share some of the fun things we have done and help you plan the perfect Chicago itinerary.

Let's plan a weekend Chicago trip summer itinerary! 

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Contents show

How To Get To Chicago

Flying to Disneyland

Chicago has two major international airports. Chicago O'Hare (ORD) and Midway (MDW). If you want another option Milwaukee (MKE) is not too far from Chicago.   I love to check the price and see where I can find the best deal.

Chicago O'Hare International Airport

Chicago O'Hare is my favorite airport to fly into.  It is just north of Chicago.  It is a safe area.  You can easily grab an Uber or rent a car.  


Midway is the Southwest Airlines Hub.  If you are a loyal Southwest flyer this is where you will want to book through.  Midway is south of downtown Chicago.  Anything in South Chicago is dangerous. However, the police patrol the area near the airport to the interstate.  You will be safe getting to downtown.  

I have flown into both of these airports and honestly, I usually book where I can find the best deal. However, I really like O'Hare and the area it is located in better than Midway. 

Best Places to Stay in Chicago

Weekend in Chicago Summer at the River

Summer in Chicago is a great time to walk around the city, and finding a great hotel within walking distance of the Chicago attractions is very convenient.  

Best Hotels in Chicago

If you want to stay in Downtown Chicago there are a few areas I recommend. The Magnificient Mile and Riverwalk areas are close to all the Chicago attractions.  

Magnificent Mile

River Walk

There are some great hotel options in Chicago. Marriott brands are my favorite but Chicago actually has lots of amazing hotel brands to choose from! 

Plan your Weekend Chicago Trip Itinerary

Chicago Summer 3-day Chicago Itinerary - Navy Pier

Chicago in the Summer is the best time to visit.  Let's list all the things to do in Chicago in Summer. 

You can pick and choose which items you want to add to your weekend in Chicago itinerary! (Or as I said earlier you can easily plan a longer Chicago itinerary)

1. Go To A Cubs Game

Chicago Itinerary - Chicago Cubs Games

Chicago is a city that comes to life in the summer. One of the best ways to experience Chicago during the summertime is going to a Cubs game at Wrigley Field.

Wrigley Field is one of the most iconic baseball stadiums in America, and going to a game there is a must-do for any sports fan.

Even if you’re not a big baseball fan, the experience of being in such a historic stadium is worth it. The vibe at Wrigley is electric, and it’s easy to get caught up in the excitement. Plus, there’s nothing like enjoying a cold beer and a hot dog while watching a game on a summer afternoon.

Chicago Traditions

One of the best things about going to a Cubs game is that you get to experience some of the long-standing traditions that happen at Wrigley Field. During the seventh-inning stretch, fans and a celebrity guest join to sing “Take Me Out To The Ballgame.” When the Cubs win, fans celebrate by singing “Go, Cubs, Go” and proudly waving their white flags with a blue “W” signaling the team's victory.

You can purchase your Cubs tickets on the official MLB website or a third-party site. Games begin in early April and go through October.

Contributed By: A World In Reach

2. Chicago River Cruise

Chicago is a towering city with over 130 years of modern history, and a visit there without noting the architecture is incomplete.

Winding its way through the city, crossed by dozens of bridges, is the ever-present Chicago River. So, there is no better way to really appreciate the city than to take a cruise along the river, admiring and learning about the famous buildings along the way. The tour will especially appeal to architecture buffs, but no matter what your interests, you’ll enjoy the cruise.  

Chicago River Cruise Boat Tours

There are several boat operators, but there are typically three types of cruises. 45-minute cruises stay in the heart of the city, where there’s the largest concentration of buildings and most points of interest. 90-minute cruises venture further along the river, taking in more sights.

There are also cruises that not only go along the river, but also for a spin out into Lake Michigan. This gives you a wonderful panoramic view of the whole city. 

The 90-minute Chicago River Architecture Tour and the Lake & River Architecture Tour (also 90 minutes) cost $42 for adults and $19 for children 4-12. Under 4s are free. The 45-minute Chicago River Architecture Cruise is $25/ $10. They run frequently throughout the day from around 9:30 am to 9:00 pm. 

Contributed By:  Travel Collecting 

3. Navy Pier

Navy Pier - Chicago Itinerary

If you’re visiting Chicago in the summer, you won’t want to miss the fireworks that happen at Navy Pier. Starting May 28 and running through Labor Day, the fireworks happen every Wednesday and Saturday.


The fireworks start at 9:00 pm on Wednesdays and 10:00 pm on Saturdays. You can view these fireworks on a sailboat tour to make it extra special. 

One of our favorite spots for watching the show is from a boat on Lake Michigan. It’s beautiful to see the Chicago skyline lit up from the water and hear the oohhs and aahhs from other boats. Everyone from toddlers to grandparents are sure to enjoy this experience!

If you would rather watch from the shore, try going on the Centennial Ferris wheel during the show, or have dinner at one of the Navy Pier restaurants and enjoy a front-row seat.

Whether you’re planning to visit Chicago with grandparents this summer, or heading off on a romantic weekend Chicago getaway, we’re sure you will love every minute exploring the Windy City!

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4. Willis Tower - Top Chicago Itinerary Item

Willlis Tower Chicago Itinerary

103 floors above Chicago’s streets you will either be terrified or amazed at the views of The Willis Tower, a 1450-foot skyscraper in Chicago.

The tower has 108 stories and was the tallest building in the world for 25 years. You’re going to want to do the best part which is stepping out onto The Ledge of Skydeck, the highest observation deck in the United States. It’s basically a glass box on the 99th floor of Willis Tower.

When people ask me about things to do in Chicago with kids, I always tell them about the breakfast we had at sunrise in the Willis Tower, a must-do experience. If you can’t visit for sunrise then your next best time of day is sunset. Even if you want to catch the twinkling lights of Chicago go just before the sunset so you can still see the magnificent city of Chicago in the golden sun glow.


Admission for 12 and up is $30 – $44, 3 to 11-year-olds are $22 – $36, and under 3 is free. Check the website for opening hours, as they change seasonally and during holidays but most days you can go anywhere between 9 am and 10 pm.

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5. Eating Deep Dish Chicago Pizza

Chicago Summer Deep Dish Pizza
You cannot go to the Windy City any time of year without eating Chicago deep-dish pizza! Invented in 1943 at Pizzeria Uno, this is Chicago’s most famous food. And because it’s so well known, you’ll see lots of pizza places advertising for it. But don’t settle for any Chicago pizza, make sure you try an authentic deep-dish. 
As the name infers, Chicago-style pizza is made in a deep iron skillet or pan and baked. If you’ve never had deep-dish pizza, it looks more like a savory cake than a pizza with a layer of sauce on top. The pizza is basically constructed upside down with the toppings on the crust, then massive amounts of cheese, and then the sauce. You will never have a pizza with more cheese!

Pizzeria Uno

You can try Chicago’s iconic dish at the original Pizzeria Uno location at 29 East Ohio St, but nowadays, a few other local spots rival for the best Chicago pizza. Lou Malnati’s Pizzeria, Gino’s East, and Pequad’s all serve a delicious authentic deep-dish you’ll love! You can actually go on a Chicago Pizza Tour
This is the perfect addition to your weekend Chicago trip itinerary! 
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6. Historic Route 66

Summer in Chicago - Start of Route 66
Chicago has so many wonderful things to do that it can be difficult to fit all of your must-dos into a three-day Chicago itinerary. However, eating breakfast at the beginning of Historic Route 66, at Lou Mitchell's diner, is an easy addition. 

Start of Route 66 – Lou Mitchell's 

Most people don't realize that the beginning point of Route 66 in Chicago has changed over the years. While the sign currently says Route 66 started on Jackson Blvd and Michigan Avenue, the historic highway originally started in 1926 on Jackson Boulevard right in front of Lou Mitchell's. The diner opened in 1923.
Lou Mitchell's has some of the best breakfast food in Chicago. On weekends, the line can wind around the block for visitors who arrive after 10 am. If you do wait in line, don't fret. The host serves homemade donut holes to diners while they wait in line. 
Lou Mitchell's opens at 6 am on weekdays and at 7 am on weekends, and closes at 2 pm daily. So get there early to ensure you don't have to waste time waiting in line during your three-day Chicago itinerary.
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7. Lake Shore Drive

Lake Shore Drive Chicago Itinerary

Renting a Divvy and biking down the Lakefront Trail is one of the best things to do in Chicago on a summer day. Once the weather warms up, Chicagoans and tourists alike head outside to enjoy the gorgeous scenery and sunshine.

Divvys are Chicago’s bicycles that are available to the public to rent. There are more than 100 rental stations scattered all around the city, so finding a free bike is easy. They can be unlocked using the Divvy app. There are 1 ride, 1 day, and annual memberships available. The prices are quite reasonable — for a single ride, it costs $1 to unlock plus $0.16 a minute to ride.

Lakefront Trail

There are many different trails to bike around the city, but one of the best has to be the Lakefront Trail. Lakefront Trail North and Lakefront Trail South run along the shores of Lake Michigan, parallel to Lake Shore Drive.

Along the trail are some of the greatest skyline views of downtown Chicago. The trail also passes several other major attractions, including North Avenue Beach and Belmont Harbor.

Most travelers would enjoy a Divvy ride in the summer. It’s inexpensive and a great way to see the city while enjoying the beautiful weather.

It is one of the best things to add to your weekend in Chicago trip itinerary! 

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8. Summer in Chicago - Lake Michigan

Speed Boat Cruise Lake Michigan

Lake Michigan is one of the best places to visit on a Chicago summer day.  There are so many amazing things to do on Lake Michigan.  

We have been on the speed boat cruise and it was amazing! It was so fun! I would do it over and over again!  It is worth booking and adding to your weekend in Chicago itinerary! 

9. Hop On Hop Off Bus Tour - A Chicago Itinerary Must!

One day in Miami hop on hop off bus tour

My favorite way to see any city is by a hop-on hop-off bus tour.  I feel like you get a really good overview of what the city has to offer.  

I think these bus rides are really relaxing, you don't have to walk as far to see the things you really want to see! This is a great option to add to your weekend in Chicago trip itinerary! 

Chicago at Night

There is a Chicago at Night Bus tour that is perfect if the Chicago summer day is too hot! It will be a little cooler in the evening.  This is a great way to explore the city! 

Chicago Crime and Mob Bus Tour

Chicago has a reputation for organized crime.  If this interests you, you can also take a Mob Bus Tour and learn about the city's mobs. There is also a Chicago Night crimes bus tour to check out.  Another great option is the Gangster Tour Bus Tour.  

10. Visit the Chicago Museums

Museums in Chicago

Chicago has the best museums!  They are some of the best in the entire United States.  

You need to check out any of the following maybe even one each day of your weekend in Chicago trip. 

We have been to all of these museums and love them. Even if you are short on time be sure to add at least add one to your 3-day Chicago itinerary! 

If you plan on doing two or more of the museum or touristy sites during your weekend in Chicago, I highly suggest getting a City PassIt is super convenient. 

Hot Tip

If you have a museum pass in your home state check to see if they are participating in the ASTC program.  We usually get into the Science and Technology Museum for free with our local museum pass. 

11. Magnificent Mile

Magnificient MIle Chicago Itinerary

The Magnificent Mile is the best shopping area ever! It actually is one of the most famous shopping areas in the world.  

You will find designer storefronts and also great restaurants.  This is where everyone loves to go in Chicago in Summer.  In fact, a walking tour is perfect so you can explore all the cool things in this area. You could also do a fun scavenger hunt of the area. It should be at the top of your weekend in Chicago list! 

American Girl Store

If you have young girls the American Girl Store is a must! Make sure to make an apt for you and your doll.  It is a perfect thing to add to your family's Chicago itinerary.

12. Taste of Chicago - Food Tours

Chicago Summer food tour

Chicago has some amazing food tours! Booking a food tour is an experience that you will want to include on your weekend in Chicago trip itinerary! 

Taste of Chicago

If you visit Chicago in the Summer you can attend the Taste of Chicago.  It is a foodie event that has been around for over 40 years. 

Every weekend leading up to the main Taste of Chicago event on the Lakefront there are different venues where you can get a “taste” of what the big celebration will be like.  Taste of Chicago brings in amazing restaurants and provides concerts and dances.

Food Tours

If your weekend in Chicago is not during one of the pop-up locations or the main event in July, you can take a private food tour. 

One of the best is the Underground Donut Tour. There are also traditional food tours and even specialty food tours experiencing the best foods in Chinatown, Wicker Park, and Mexican cuisine.

Adding a food tour to your weekend in Chicago itinerary is a great idea and an experience you will not forget!  

13. Millenium Park

Millinium Park Chicago summer

Millennium Park is a must for your Chicago summer vacation.  It is a park built entirely on top of a parking garage!  The iconic “bean” is one of the city's most famous landmarks.  

The park is safe and a fun place to visit and get an instagramable shot with the bean! You can also take a self-guided tour and learn all about the area. 

14. Chicago Summer Music Festivals

Chicago Summer Outdoor Music Festivals

Chicago summer nights are the best time to catch a live concert. There are so many music festivals in Chicago throughout the summer. 

Big Chicago Summer Festivals

  • Lollapalooza
  • Suenos Music Festival
  • Hyde Park Summer Fest
  • A Day in the Country Music Festival
  • Windy City Smokeout Festival
  • Lyric Lemonade Smash Party

There are a lot more music festivals all summer long.  The largest festival is Lollapalooza.  If your weekend in Chicago trip falls when a concert is being held this would be a great item to add to your 3-day Chicago itinerary.  

15. Chicago Ghost Tours

Chicago Ghost Tour

Ghost tours are a thing in every big city.  There are lots of options to choose from.

Ghost Tours in Chicago

Ghost hunting is a great activity for a Summer Chicago night! These are also available during the day but how cool would it be at night!

16. Chicago Theater

Chicago Theater

I know a weekend in Chicago trip itinerary for me would include a Chicago Broadway production.  I love the theater.  I have been many times in Chicago.  

2022 Chicago Summer Line 

I can honestly say every time I have seen a show in Chicago it was just as good as my New York experiences! 

17. and 18. Lincoln Park Zoo and Brookfield Zoo

Chicago Zoo

There are two zoos located near Chicago.  They are both great Chicago summer activities to add to your weekend in Chicago itinerary.

Lincoln Park Zoo

Lincoln Park Zoo is one of the 4th oldest zoos in the United States and is one of the only few to offer free admission.  Lincoln Park Zoo is about a 7 to 14-minute drive from downtown Chicago.  


Weekdays: 8:00 am – 5:00 pm 

Weekends: 8:00 am -7:00 pm 

Brookfield Zoo

Brookfield Zoo is located in Brookfield, IL. Depending on traffic it can take anywhere between 25- 55 minutes from downtown Chicago to arrive.  

Hours and Admission

Adults: $24.95

Children: $17.95

Hours: 10:00 am – 5:00 pm

19. Chicago Air and Water Show

Chicago Air Show

If you are around at the end of a Chicago Summer.  The Chicago Air and Water show is a must! 

Free Event

One of the best things about this show is that it is FREE!  It is such a fun event to check out! It typically happens in August.

20. Medieval Times

Medieval Times

Now, Medieval Times is not unique to Chicago, however, there is a location about 35 minutes to 1 hour depending on traffic from downtown Chicago.

Medieval Times Show

Medieval Times is a cool show.  You become members of a house and get to cheer on your knight in shining armor.  Dinner is served while you watch a fabulous show your whole family will love.  My family loved it! 

If your weekend in Chicago includes kids, this is a fun option! 

21. Six Flags Great America

Things to do in Gurnee Illinois - six flags

Six Flags Great America is one of the many things to do in Gurnee, Ilinois.  It is located about 40 minutes north of Chicago.  

This is one of the best Six Flags ever! It is so fun with some of the best rides! This is the perfect day trip from Chicago.  What is great about this Chicago summer venue is that there is a water park inside of Six Flags!

Admission and Hours

Hours: 10:30 am – 8:00 pm

Adults and Children: $34.99

This is a fun family Chicago activity to check out on your weekend in Chicago trip! Honestly, you probably need 1 week in Chicago to really be able to include this in your Chicago itinerary. 

22. Lego Discovery Center

Lego Discovery Center - Chicago

We have some huge Lego fans in our house.  We have been to Legoland in California and a few of the Legoland Discovery Centers located in Dallas and this one located in Chicago.

The Lego Discovery Center is actually located about 40 minutes west of downtown Chicago.  The Lego Discovery Center offers fun rides, free build locations, and is perfect for any little Lego lover.

Admission and Hours

Adults and Children: $24.95

My little kids loved this. One thing that is really nice is that located a few doors down is an arcade.  So if you have a family with both little kids and teens you can divide up and accommodate both age groups.  

23. Morton Arboretum

3 day chicago itinerary - Trolls Mortan Arboretum

If you want to have a unique experience in Chicago, head to the Morton Arboretum. 

The arboretum is located about 40 minutes west of downtown Chicago.  What makes this place so special is that you will literally get to hunt for gigantic trolls.  They are located all around the arboretum. 

 It is a really beautiful way to get out on a Chicago summer day and the perfect thing to add to your Chicago itinerary! 

Admission and Hours

Adults: $16

Children: $11

Hours: 7:00 am – to Sunset

24. Great Wolf Lodge

Best family resorts in the world - Great Wolf Lodge

Great Wolf Lodge is one of the best family-friendly activities in Chicago.  It is located near Six Flags in Gurnee, Illinois.  (about 40 minutes North of the city)

Great Wolf Lodge is a kid's dream.  This hotel experience includes an indoor water park, a magic quest adventure, and many many fun activities! 

Great Wolf Lodge Activities

  • Water Park
  • Magic Quest
  • Bowling
  • Rock Climbing
  • Mini Golf
  • Arcade
  • Build A Bear

The rooms are really nice and spacious! If you want to turn your 3-day Chicago itinerary to a 5-day Chicago Itinerary heading north and visiting both six flags and Great Wolf Lodge is a great addition to your Chicago itinerary! 


25. Best Chicago Beach

Chicago Beach Summer Chicago Fun

Hitting the beach?  Yes, you can enjoy a day at the beach in downtown Chicago! Crazy, Right?!! There are over 24 different beaches that are open in Chicago in the Summer.  The best part is they are all free! 

There are a few great Chicago beach options to choose from.  The most popular beach is Oak Street Beach.  This beach offers great restaurants, a spectacular view, and even sand volleyball.

Popular Chicago Beaches

  • Oak Street Beach
  • North Avenue Beach
  • 12th Street Beach
  • Montrose Beach
  • Ohio Street Beach
  • Fullerton Beach

26. Maggie Daley Park

Maggie DAley Park - Chicago Itinerary

Maggie Daley Park is a must if you want to have a fun day enjoying Chicago.  This park has it all! There are so many fun things, especially for kids! 

Things to Do at Maggie Daley Park 

  • Climbing Wall
  • Garden
  • Play Garden 
  • Tennis Court

This is such a fun place but only if you have extra time on your weekend in Chicago trip! 


Weekend Chicago Itinerary Ideas

Downtown Chicago Itinerary

I thought I would put together a couple of 3-day Chicago itinerary choices and maybe a  4-day Chicago itinerary option.  Honestly, you could make your weekend Chicago trip into an entire 1 week Chicago itinerary.  

Traditional 3-Day Chicago Itinerary

Family 3-Day Chicago Itinerary

Day 1 

  • Explore Navy Pier 
  • Check out Lake Michigan (boat ride)
  • Pick one Museum
  • Chicago Broadway Play

Day 2 

  • Hop-on Hop-Off Bus Tour
  • Magnificent Mile
  • River Boat Cruise
  • Pick one Museum
  • Millennium Park

Day 3

  • Bike Lakefront Trail
  • Food Tour
  • Willis Tower
  • Cubs Game (or Concert)

Day 1

  • Navy Pier (Ferris Wheel)
  • Children's Museum
  • Speed Boat Ride
  • Willis Tower
  • Try Chicago Pizza

Day 2 

  • Bike Riding on Lakefront Trail
  • Millenium Park
  • Shedd Aquarium
  • Lego Discovery Center
  • Medieval Times

Day 3 – 4

  • Six Flags
  • Great Wolf Lodge

Are you Ready for a Weekend Chicago Trip?

Weekend in chicago itinerary building

Hopefully, this helps you plan a perfect Chicago Summer trip!  I know your weekend in Chicago itinerary will be amazing!  

Chicago is such a fun city with so many awesome attractions!  Tell us all about your trip in the Facebook Group! 

General Travel Facebook Group

If you have any questions join my Facebook Travel  Community.  You can ask any questions you have about upcoming trips and everyone is happy to help you plan your trip.  I also try to give exclusive travel deals that companies send me.  It is a great group to join!

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  1. I’ve been to Chicago a couple of times, both for courses/training, so I haven’t been able to explore nearly as much as I’ve wanted to. I did get to go to a Cubs game, visit Millenium Park, try some yummy pizza and stroll around Navy Pier. Looks like I need to go back and try some of these other activities! Can’t wait 😊. Xx Sara

  2. Great tips for a fab stay in Chicago! The best parts for me look like the bike trails and the food tours. 🙂

    p.s. I love the photo of you all jumping in Willis Tower!

  3. I’m looking forward to getting back to Chicago in the summer. We were there in December which was a bit different for a couple of Aussies!

  4. This is the perfect article to plan your visit to Chicago! There is so much to see and this is very helpful to plan your time and get the best out of it! Thanks for sharing this article! I can’t wait to visit!

  5. Woah, I’m spoilt for choices – who would’ve thought there’d be so much to do in Chicago! One weekend doesn’t seem enough time! Thanks for sharing!

  6. What a great weekend in Chicago trip itinerary. We’ve had lots of visits to Chicago and have done at least half of these things! Great variety and great tip about the museum membership program too!

  7. Amongst the tops Chicago Activities I would have to eat Deep Dish Pizza first. Then I would head over to a Chicago beach.

  8. I haven’t been to Chicago yet, looks like there is lots to do. I think it’s time to plany a weekend Chicago trip.

  9. I’ve never been to Chicago and I never realized how much there is to do there! I would love to catch a Cubs game and go on a food tour. Deep Dish Pizza? Sign me up! I’ll definitely be referring to your recommendations when I go to plan a weekend there.

  10. This is an amazing guide! So many tips and so well organized, I really enjoyed reading it! I would love to visit Chicago, I have only stopped there once because of a medical emergency on a plane, but it would definitely make a great destination! I would love to do a boat trip on the river and try the Pizza! Thanks for sharing!

  11. I love that you went through everything and then did a summary bullet point itinerary at the end – it makes everything so easy to digest at the end of it all and definitely easier for planning purposes!

  12. Chicago is still on my list of cities to visit in America! It looks amazing, with so many options for things to do. Thanks for the great tips!

  13. Chicago is such a fun city! We love the views from the Aquarium. Thanks for this Chicago Trip Itinerary!

  14. We took my oldest kid to Chicago for a few days, but we haven’t been since the youngest was born, and that was almost 13 years ago! We need to go back. We did the museums mostly, and we had a great time. I love ghost tours, so I’d definitely want to check that out. Hopefully, we’ll get back there soon!

  15. Love this weekend planning guide to the top summer things to do in Chicago. I’ve been to the Windy City many times and love it…but you have a few things on your list that I need to experience.

  16. Chicago is so vibrant with lots of things to do and see. There were some on the list that we didn’t even think of. Thank you for sharing all of the activities that can be done.

  17. I love Chicago. I have been there many times both as a child and adult. All wonderful! Thanks for the great ideas on where to go.

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