Trip report

Question

Wanted to share our weekend experience (2 weekends ago). Was an 86 birthday celebration for my mom, brought my daughter too. Got in to O’Hare 1:30, found the map for the Blue line. Another single woman was looking rather nervously so we told her to join us and we’d all figure it out together. Ended up having a fun late lunch with her, met a new friend, exchanged info! Checked in to Courtyard Marriott on Hubbard, great location, and went out for dinner to Blue Sushi, very good and excellent Bluetini. Next morning took the water taxi to Chinatown, walked around, ate, shopped a good bit, back to the room for a rest then dinner at Birdman Ramen, funky place, good food. Walked more of the MagMile. Sunday morning went to Art Institute, fabulous. My 86-yr old mom walked all the way back to our hotel, she’s amazing! Anyway, great weekend, Chicago has so much to offer, can’t wait for our next trip.

Answer

Thank you for sharing your Chicago weekend trip report! It sounds like a fantastic way to celebrate your mom’s 86th birthday with a mix of sightseeing, dining, and fun adventures. Chicago really offers something for every interest, from cultural landmarks to quirky restaurants and unique experiences.

Arrival and Transit

Arriving at O’Hare at 1:30 p.m. and navigating the Blue Line is a convenient and budget-friendly way to reach downtown Chicago. It’s great that you connected with another traveler and made a new friend along the way — one of the unexpected joys of city travel.

Accommodations

Staying at the Courtyard Marriott on Hubbard Street is an excellent choice. Central downtown location, easy access to major attractions, and comfortable lodging for a multi-generational group.

Dining Highlights

Blue Sushi: Excellent for sushi lovers, especially with their signature cocktails like the Bluetini. Perfect for a late dinner or evening drinks.
Birdman Ramen: A funky, casual spot with good ramen and a relaxed atmosphere. Great for dinner after a day of walking and sightseeing.

Sightseeing

Water Taxi to Chinatown: A fun and scenic way to explore, avoiding the busier streets and seeing Chicago from the river. Chinatown offers excellent walking, shopping, and casual dining.
MagMile Shopping: Ideal for catching stores along Michigan Avenue, from high-end boutiques to fun souvenir shops. Walking is manageable if you pace yourself and rest in between.
Art Institute of Chicago: A must-visit cultural landmark with world-class collections. Your mom’s walk back to the hotel is impressive, showcasing her stamina!

Tips & Takeaways for Future Trips

Chicago has great public transit options — Blue Line and water taxis are both convenient, especially when traveling with family.
Mix cultural activities (museums, art, architecture) with lighter, fun experiences (Chinatown, restaurants, MagMile) to keep everyone engaged.
Plan for rest periods in between sightseeing to accommodate older travelers.
Trying local, casual, and quirky restaurants adds unique flavor to the trip — don’t miss sushi, ramen, and cocktails.
Walking can cover a lot of downtown Chicago, but comfortable shoes are essential.

Overall, your weekend captures the perfect balance of exploration, family celebration, and culinary adventures. Chicago’s mix of culture, architecture, and vibrant neighborhoods makes it an ideal destination for multi-generational trips. Planning similar itineraries in the future with a mix of structured and spontaneous activities will ensure another memorable experience.

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