Weekend trip with Tweens

Question

Hello!

We are doing a mother/ daughter trip with 12 and 13 year old next weekend. Have lots of ideas for daytime activities- shopping, boat tour, parks, etc., but what about evenings? Any restaurants or other ideas that would be fun for tweens?

Thanks in advance!

Answer

Chicago has a lot to offer for evening activities with tweens, combining food, entertainment, and unique experiences. Since your daughters are 12 and 13, you’ll want options that are fun but age-appropriate, and ideally not too far from your daytime activities in the city.

Here are some restaurant suggestions and evening ideas:

Restaurants:
- Giordano’s or Lou Malnati’s – Classic Chicago deep-dish pizza that kids often love. Casual, fun atmosphere.
- Portillo’s – Chicago-style hot dogs and Italian beef sandwiches. Quick, casual, and fun for teens.
- Rainforest Cafe – Themed dining experience with animatronic animals and tropical décor. Entertaining for tweens.
- The Gage – Located near Millennium Park, a more relaxed sit-down option with diverse menu items that appeal to families.
Evening Entertainment:
- Millennium Park at Night – See the Cloud Gate (“The Bean”) lit up, and enjoy walking around the park. Often quieter in the evenings.
- Chicago Riverwalk – Scenic stroll along the river, sometimes with street performers. Great for photos and a casual evening walk.
- 360 Chicago Observation Deck – Visit the John Hancock building observation deck for nighttime city views. They also have the TILT experience if your tweens like a thrill.
- Chicago Architecture Boat Tour (Evening Options) – Some operators offer twilight or sunset tours, giving a different perspective on the city’s skyline.
- Indoor Activities – Consider escape rooms suitable for tweens, bowling alleys, or an indoor mini-golf venue like Urban Putt.
Other Fun Ideas:
- Maggie Daley Park – Evening visits can be magical if there are still open play areas or climbing structures.
- Ice Cream or Dessert Stops – Places like Jeni’s Splendid Ice Creams or Little Goat Diner can be a sweet end to the day.
- Live Shows – Look for family-friendly theater or improv shows that allow younger audiences, like at Second City’s kid-friendly performances.

Tips:

Evenings in Chicago can be busy downtown, so plan transport (CTA, rideshare, or walking) accordingly.
Check closing times; some attractions may close earlier on weekends or in August.
Combining a fun dinner with a nearby evening stroll or activity is a great way to maximize time and keep the day relaxed but exciting.

Overall, a mix of casual dining, a scenic walk along the river or park, and a unique city experience like an observation deck or themed restaurant can make the evening memorable for tweens while keeping it easy for adults too.

Weekend trip with Tweens

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