Hannah & Allen

Hannah & Allen

May 24, 2025 • Chicago, IL
Hannah & Allen

Hannah & Allen

May 24, 2025 • Chicago, IL

Our Chicago Favorites

If you’re making a weekend out of it, here are some of our favorite spots—whether you want to check out classic Chicago sights, grab a great meal, or just have a drink with a view.

Chicago River Architecture Boat Tour

Picture of Chicago River Architecture Boat Tour

One of the best ways to see the city. This boat tour takes you through downtown along the river, with some solid skyline views and a little history thrown in. Grab a drink, sit back, and enjoy the ride.


Cubs Game at Wrigley Field

Picture of Cubs Game at Wrigley Field

If you’re still around on Monday, there’s a Cubs game at 1:20 PM. Whether you’re a die-hard fan or just here for the beer, Wrigley is always a good time.


📍 Game Date: Monday, May 26 @ 1:20 PM

Our Favorite Rooftop Bars & Restaurants

Allen is the KING of dining out, so after many meals, drinks, and rooftop sunsets, we’ve rounded up our absolute favorite spots in Chicago.


Best Rooftop Spots

- London House

- Cindy’s Rooftop

- Miru Rooftop

- Nobu Rooftop


Favorite Lunch & Dinner Spots:

Casual Favorites

- Lux Bar

- Tavern on Rush

- Parlor Pizza

- Pizzeria Portifino

More High-End

- Chicago Cut Steakhouse (Allen's favorite)

- Gibsions Italia (Hannah's favorite)

- Beatnik on the River

- Le Colonial

- Francesca's


Favorite Bars:

- Butch McGuire’s (Irish Pub)

- Red Head (Piano Bar)

- Zebra Lounge (Piano Bar)

- Bub City (Live Music)

- Texan Taco (Live Music)

- Three Dots and a Dash (Speakeasy)

SHOPPING & EXPLORING

Chicago Riverwalk – Perfect for a walk, drink in hand, and looking at boats on the river


Michigan Ave / Magnificent Mile – Great shopping and restaurants


West Loop / Fulton Market – Trendy area with great food and bars


Navy Pier – Classic Chicago views, drinks, and restaurants. If you’re feeling ambitious, Soaring Through Chicago is a ride that gives a full aerial view of the city.