Ashlyn & Benjamin
Things To Do
Christkindlmarket Chicago
Located in Daley Plaza, this traditional German Christmas market is a Chicago staple. It’s the perfect place to grab a souvenir mug, enjoy some spiced wine, and browse handmade holiday crafts.
Willis Tower
If you want to visit the site of our engagement and get the best view of the city, look no further! On the 103rd floor of the Willis Tower, step out onto the "Skydeck", a glass balcony that extends outside the building for a view straight down to the street below.
Field Museum
One of the premier natural history museums in the world! It’s home to SUE, the world's most complete T. rex. A great way to spend a few hours exploring history and science near the lakefront.
The Art Institute of Chicago
The Art Institute displays an overwhelming collection of works for all types of art lovers, including masterpieces like Georges Seurat’s A Sunday on La Grande Jatte, famously featured in Ferris Bueller's Day Off.
Cadillac Palace Theatre
Located next door to The Allegro Hotel Chicago Loop. Check back closer to 12/12/2026 to find what show will be touring! We encourage you to also browse the many other theaters the Chicago Theatre District has to offer.
Pequod's Pizza
Pequod's Pizza specializes in Chicago deep-dish pizza with a caramelized crust. It’s a bit far from the hotel, but the pan-style pizza is well worth the trip. We suggest grabbing a reservation!
Geja's Cafe
This is one of our favorite spots in the city! We come here every year for our own "Christmas in Chicago" celebration to enjoy fondue, wine, and live music. We suggest grabbing a reservation!