Chicago in late May is a wonderful time to visit, typically mild, mostly sunny weather with daytime highs in the 60s–70s and long daylight hours perfect for exploring.

📍 Iconic City Favorites

• Millennium Park & “The Bean”

Photos, art, and outdoor space right downtown.

• Willis Tower Skydeck

Amazing skyline views from the top.

• Architecture Boat Cruise — Bride Favorite

Classic Chicago experience — learn about the city’s famous buildings from the river.

• Chicago Riverwalk

Beautiful stroll with restaurants, drinks, public art, and views of the city.

🎨 Museums & Culture

• Art Institute of Chicago — world-class art and rotating exhibits.

• Shedd Aquarium & Adler Planetarium — great indoor options if the weather changes.

• The 606 / Bloomingdale Trail — elevated urban trail perfect for a walk or bike ride.

🎉 Events Around The Wedding Weekend

• Belmont-Sheffield Music Fest (May 22–24, 2026) — live music, local vendors, beer garden vibes.

• Chicago Memorial Day Parade (May 23, 2026) — downtown parade to kick off the holiday weekend.

• Navy Pier Fireworks — summer fireworks begin right around your weekend and continue through the season.

• Street and food fest fun — including Division Street Fest, Hot Dog Fest, Lincoln Park Mayfest & more near late May.

🍽️ Food & Drink Highlights

• Chicago classics: deep-dish pizza, Italian beef sandwiches, Chicago-style hot dogs.

Pizza picks from the bride and groom: Pequods, Pizzeria Uno

• Outdoor patios, riverfront dining & rooftop bars: perfect with warm May evenings.

🚗 Getting Around: Uber & Lyft

Chicago is very rideshare-friendly, Uber and Lyft are available citywide, which makes getting between activities quick and easy if you’re not familiar with public transit or walking routes.

• First-time riders:

If you haven’t used Uber or Lyft before, you can enter a referral code in the app (during signup or in “Promos/Rewards”) to get ride credits or discounts on your first ride. It’s a great way to save on airport transfers or sightseeing trips. If you need a referral code, feel free to ask the bride or groom—they’re happy to share one to help you get set up.