Help with June Itinerary

Question

My husband, myself and my daughter (17) will be traveling to Chicago June 7-15. My husband has only been there for work and it will be the first trip for my daughter and myself. Please make suggestions on my rough itinerary. My husband will be working Mon, Tues and Wed and has a meeting Friday morning. We will also be celebrating my birthday while we are there (June 10).

June 7 -- Arrive O'Hare Airport around 11 am. We are staying the first half of our trip at hotel convenient for Husband's work somewhere around Des Plaines and Glenview. We want to drop our bags and head downtown to Navy Pier, walk around, ride the ferris wheel and do a river cruise.

June 8 -- HOHO bus tour. Not sure where we will hop off yet, we will play it by ear I guess.

June 9 -- Art Institute of Chicago and a self guided walk around Millennium Park.

June 10 -- Maybe a beach day at Oak Street Beach or North Avenue Beach where we can rent chairs and umbrellas and relax for the day. Evening -- Titanique or Second City??

June 11 -- Today we move hotels to Hyatt Place River North for the rest of our stay. Lincoln Park Zoo, Wicker Park, Bucktown

June 12 -- Chicago River Walk and History tour. Afternoon/early evening -- Some kind of walking food tour to try deep dish pizza, Italian Beef, etc.

June 13 -- Magnificent Mile, shopping, one of the observation decks (any preferences??)

June 14 -- ???

June 15 -- ??? We leave around dinnertime to fly back to Houston.

I know we have some gaps and still trying to figure out what to do. Maybe another museum like the Chicago History Museum or the Adler Planetarium. My daughter and I like to wander neighborhoods stopping in at cute boutiques, bookstores and vintage/resale shops... what neighborhoods would you recommend for that? We also like to wander in historic churches/synagogues.

If we do end up with an extra day, any day trips from Chicago that you would recommend that we can reach easily by train?

Thanks!!

Answer

It sounds like you have a wonderful trip planned to Chicago, with a good mix of activities for your husband, daughter, and yourself! I’m happy to offer some suggestions for your itinerary, especially for the days when you have more flexibility. I’ll also provide recommendations for neighborhoods to explore, museums, and day trips, along with ideas for filling in the gaps in your schedule.

June 7 – Arrival and Navy Pier
Your first day in Chicago sounds like a great introduction to the city. Since you'll be staying near Des Plaines and Glenview, it’s smart to head downtown to Navy Pier. In addition to the ferris wheel and the river cruise, you can explore the Pier itself, which offers attractions like the Centennial Wheel, the Chicago Children’s Museum, and restaurants with views of Lake Michigan. If you have time, consider a visit to the nearby Chicago Shakespeare Theater or a relaxing boat ride along the lakefront.

June 8 – HOHO Bus Tour
A hop-on, hop-off bus tour is an excellent way to get a feel for the city, especially with the flexibility to choose which attractions interest you most. Some great stops might include the Magnificent Mile, the Museum Campus (home to the Field Museum, Shedd Aquarium, and Adler Planetarium), or Lincoln Park Zoo. Since you’ll be playing it by ear, I’d suggest taking some time to stop at a neighborhood or two for boutique shopping, especially in the Wicker Park area (which you’ll visit later) or the Gold Coast for its upscale shops and charming streets.

June 9 – Art Institute and Millennium Park
The Art Institute of Chicago is a must-see for any art lover, and it’s also a great museum for a first-time visitor since it has such a broad collection, from ancient to modern art. Afterward, a self-guided walk around Millennium Park is a great idea! Be sure to stop by the Cloud Gate sculpture (aka "The Bean"), the Crown Fountain, and the beautiful Lurie Garden. You can also visit the nearby Pritzker Pavilion for live music if you time it right.

June 10 – Beach Day and Evening Entertainment
A beach day at Oak Street or North Avenue Beach sounds perfect for a relaxing birthday celebration. Both beaches are beautiful, with great views of the skyline. Oak Street Beach is a little closer to the city center and has convenient amenities. For your evening entertainment, Titanique is a fun, campy option, especially if you enjoy a mix of humor and musical theater. However, if you're more in the mood for improv and Chicago-style comedy, Second City is iconic and an excellent choice for a night of laughs. Either way, you'll be in for a treat!

June 11 – Lincoln Park Zoo, Wicker Park, Bucktown
Moving to Hyatt Place River North gives you a great base for exploring more of downtown. Lincoln Park Zoo is free and offers a lovely experience, with beautiful gardens and a wide variety of animals. Afterward, Wicker Park and Bucktown are fantastic neighborhoods for strolling and shopping. Wicker Park is known for its trendy boutiques, art galleries, and coffee shops. Bucktown offers more of the same with a laid-back vibe, and you’ll find plenty of vintage and resale shops in both areas. These neighborhoods are perfect for wandering and discovering hidden gems.

June 12 – Chicago River Walk and Food Tour
The Chicago River Walk is a wonderful way to experience the city’s architecture and history. You can walk along the river and grab lunch at one of the many riverside eateries. If you're interested in learning more about the city’s history, consider adding a guided history tour of the River Walk to give context to the stunning buildings you'll see. In the afternoon, a food tour is a great way to dive into Chicago's culinary scene. Consider a deep-dish pizza tour (Lou Malnati’s or Giordano’s are both iconic) or an Italian Beef sandwich tour. These food-focused tours are fantastic for trying local specialties and learning more about Chicago's food culture.

June 13 – Magnificent Mile and Observation Decks
Shopping along the Magnificent Mile is a great way to spend the day, especially if you like to check out designer stores and high-end boutiques. For observation decks, I’d recommend the 360 Chicago (formerly known as John Hancock Observatory), which offers stunning views of the city, or the Willis Tower Skydeck (formerly Sears Tower), where you can step out onto “The Ledge” for a thrilling view from glass boxes. Both are popular and offer great views of the city and Lake Michigan.

June 14 – Day Trip Options
If you end up with a free day, there are several day trips that you can take from Chicago by train:

Oak Park: Take the Metra train to Oak Park, a charming suburb known for its Frank Lloyd Wright homes and historic district. The Frank Lloyd Wright Home and Studio is a great stop for architecture lovers.
Naperville: A lovely suburban town about 30 minutes outside of Chicago, Naperville offers a beautiful downtown with great shopping, dining, and parks. You can also visit the Naperville Riverwalk.
Indiana Dunes National Park: If you’re interested in nature, this is a great option for hiking and spending time outdoors. It’s about an hour by train and offers beautiful views of Lake Michigan.

June 15 – Last Day
For your last day, you could visit one of Chicago's historic churches or synagogues. Consider visiting the beautiful St. James Cathedral or the Fourth Presbyterian Church near the Magnificent Mile. If you're in the mood for one last shopping spree, check out the Water Tower Place mall or visit the Randolph Street Market for unique finds.

With all of these activities, you’ll have a well-rounded experience in Chicago, balancing sightseeing, shopping, and cultural experiences. Enjoy your birthday and have a wonderful time exploring the city!

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