A Long Weekend Stay at The Robey in Chicago

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Advisor - Marisca Kooij
Curated By

Marisca Kooij

  • Chicago

  • City Travel

  • Family Travel

  • Laidback

  • High-end

  • Relaxation

A Long Weekend Stay at The Robey in Chicago
Curator’s statement

During the Fourth of July weekend of 2024, I stayed at The Robey in Chicago’s wonderful Wicker Park neighborhood. We could not have made a better choice, such a beautiful art-deco-style hotel with an amazing rooftop offering the best views of the skyline and fireworks.

The Fora Difference

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Where to stay in Chicago

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If you like interior design and architecture, you will appreciate the Robey from the moment you walk into the lobby. The use of terrazzo and wooden floors, marble, mirrors, green colors and black steel creates an authentic and warm atmosphere. They made optimal use of the flatiron-shaped structure, including the rooftop, by creating large windows in all rooms and on all sides of the building. In the rooms themselves, they used neutral colors, which creates a calm vibe. We slept in a Standard King and appreciated also having a small sitting area with a stool and sofa. Thanks to the triple-pane windows with black-out curtains, you hardly realize that you are in a lively neighborhood. In case you are used to white noise or some background music, bluetooth speakers in the room are a nice touch. For families, check out the cool, loft-style rooms with modern bunk beds.

This hotel clearly also is a favorite of the local community, which is understandable as they got so much to offer:

  • The Robey restaurant on the main floor offers “all day brunch”. If you book a room with complimentary breakfast — one of the Fora perks — this is where you will enjoy your à-la-carte-style breakfast. Many dishes have a Mexican, somewhat spicy flavor. For coffee lovers, they use a real espresso machine.

  • On the second floor, they did an excellent job in creating a space called “The Clever Coyote." Here you can do some work — the WiFi is great — and play Nintendo. Use the pool table, play shuffleboard or just have a chat and drink. Everything is possible in this mixed space.

The rooftop is split into two parts:

  1. The Cabana Club is the smaller pool area with sun loungers and also several tables to just sit, enjoy the view and enjoy the delicious, mostly Mediterranean-inspired food. In your room, you will have robes and slippers. Pool towels are provided as well. Just bring your swimsuit and sun-wear. When we were there on a Sunday morning, there was a yoga class by the pool — such a great way to start the day.

  2. On the other higher part of the rooftop, you'll find the Up Room bar with the best views of Chicago’s impressive skyline. It’s wrapped around the building and truly spectacular. Until 5 pm, access is for guests only.

Rooftop pool with high-top tables and orange umbrellas.
Skyline view overlooking train tracks with a mural of a woman's face on a nearby wall.

You certainly won’t be dehydrated when staying here. The drinks in the mini bar are complimentary. You'll find a Keurig machine in your room for coffee and tea and in the lobby there’s always cold lemon water and fresh baked cookies. It’s truly these special details as well as the super-welcoming staff that made our stay.

The active traveler would be pleased to know that the hotel offers Tokyo bikes at no additional cost as well as access to the Bucktown gym nearby. The 606 trail is only a couple of blocks away. They transformed this old railway into a fantastic 2.7-mile elevated, recreational path.

The Robey is one block from the Damen train station (blue line) and only 20 minutes by train or car to Millennium Park with the famous “Bean” sculpture — its formal name is “Cloud Gate." From there it’s great walking the Magnificent Mile, shopping and exploring the beautiful Chicago river area. Another area that we liked not too far from downtown is Fulton Market, former warehouses converted into shops, restaurants and modern office spaces.

Did you know that Chicago has over 20 amazing beaches? The water of Lake Michigan is blue and fresh and the beaches have the nicest, fine sand.

O’Hare airport is just 12 stops on the blue line, or 20 minutes by taxi. The hotel also offers valet parking for those with a car.

Skyline view of Chicago.
Skyline view of Chicago with Art Deco rooftop visible in the foreground.

Not too far from the hotel, you’ll find the greener, low-rise neighborhoods of Bucktown, Lincoln Square and Ukrainian Village — to name just a few. The many great food and shopping options might dazzle you, so much to do and see.

Need to know

I highly recommend The Robey for those who like staying outside of the high-rise, hectic downtown area and like to be in the middle of green, funky Wicker Park. Couples, groups of friends and families with older children will all enjoy the rooftop views and pool, amazing bar, games, fantastic food and the great amenities this hotel offers.

This trip report is part of our ongoing series on travel to Chicago. In need of further inspiration? Check out Marisca Kooij's guide, An Active Weekend in Sunny Sydney, Australia.

Advisor - Marisca Kooij

Travel Advisor

Marisca Kooij

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