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.
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.
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
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.
- 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
- 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)
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.