When asking yourself about something to do near me in Chicago with a group of friends or family, consider
Upstairs at The Gwen
Why Upstairs at The Gwen is a fun option when searching for things to do near me with friends and family
Upstairs at The Gwen is a modern rooftop restaurant, lounge, and bar located on the fifth floor of The Gwen Hotel in Chicago's iconic McGraw-Hill building. It offers a sophisticated yet cozy atmosphere perfect for meeting friends or celebrating special occasions. Open year-round, this destination features panoramic city views that provide a stunning backdrop from sunrise to night. Guests can enjoy masterful mixology with signature cocktails and a diverse menu of delectable American contemporary cuisine. One unique highlight is their cozy tabletop fire pits that add warmth and ambiance to outdoor seating. The venue’s design blends Art Deco inspiration with a relaxed rooftop vibe, making it ideal for socializing in style. With options for breakfast, brunch, lunch, dinner, and late-night offerings, it caters to a variety of dining preferences. Additionally, services such as valet and self-parking, reservations, public Wi-Fi, and private dining enhance the overall convenience and comfort for guests. Whether looking to indulge in expertly crafted drinks or savor flavorful dishes while taking in sweeping skyline views, Upstairs at The Gwen stands out as a premier spot to gather with friends in Chicago.
Here's what people think of Upstairs at The Gwen
As of recent, Upstairs at The Gwen holds a 4-star rating based on 371 reviews.
Reviewers consistently praise Upstairs at The Gwen for its spectacular rooftop views, attentive and thoughtful service, and a well-curated menu with excellent American fare. Many guests highlight the exceptional hospitality, especially singling out servers like Michael Ortiz for providing memorable, attentive experiences that elevated their dining. Positive reviews frequently mention the refreshing, inventive cocktails and the appealing presentation and flavors of dishes such as burgers, fries, and burrata appetizers. The ambiance, combining lively city energy and serene rooftop tranquility with cozy fire pits, also receives commendation. On the other hand, some negative feedback points to occasional pricing concerns as the venue leans toward a luxury experience, and a few guests have noted waiting times during busy hours. A minor number of reviews suggest that while the overall experience is excellent, the pace of service or seating flexibility could improve slightly. Overall, the reviews reflect a strongly favorable impression, with guests recommending Upstairs at The Gwen for both casual and special outings due to its unique combination of views, food, drink, and attentive service.
Highlights from reviewers (Most Relevant)
Scott Puccinelli
Nice outdoor terrace for dinner and/or drinks. The food was good, along with the service. (They were short staffed and the manager stepped in to help his servers, which was nice to see.) The inside area has tables and bar seating. The outside terrace has tables and couch seating, with some couches equipt with firepits. I highly recommend making reservations for either one because you can specifically reserve them, and they fill up quickly online. Food is reasonably priced for that area of the city, and so were some of the drinks. However, wine and premium liquors were very expensive. Overall, it's a great place to go.
Naz N
Had brunch at the Gwen and had a fun time. The view and seating area outside on the terrace was amazing. I ordered the Smoked Salmon & Bagel and it was delicious, highly recommend it. Nice hotel connected to the restaurant on the inside as well.
Monica Anderson
Mother’s Day Afternoon Tea- Disappointing and Not Worth the Price We brought our mom here for Mother’s Day tea and were really disappointed, especially given the high price- even more than what we paid at the Ritz a couple years ago. The event was in a windowless, undecorated room, with a DJ playing loud music that made it hard to talk. The drinks were “bottomless,” but we sat with empty glasses for 20+ minutes because the bar was “backed up”- even though the room wasn’t full. The tea kettle had just one tea bag floating inside, tag and all. The food looked nothing like the photos- no scones or sandwiches, just deep-fried snacks and grocery store pastries thrown on a tiered tray. No napkins, no linens - nothing special. Our server was sweet and did the best he could with what he had. Not his fault. But overall, this felt more like a cash grab than a luxury experience. Definitely not what you’d expect from a hotel like The Gwen.
Yanja Batbaatar
Awful awful awful!!! Avoid the high tea experience- our group left feeling scammed! Very disorganized, they had no idea what package we purchased and had to reconfirm it a number of times as well as having to remind them of our friends dietary restriction. We paid $120 A PERSON!! for some nasty boozed tea, that none of us was able to drink. Pumped with sugar and just not tasty. The tower?! Literally all deep friend and sugary snacks… we didn’t even touch it. It was supposed to be bottomless. We asked more for the savory items but they only came back with 2 of the items and said this is all they have left!!! Unacceptable On top of the $120 we paid PER PERSON! We had to order brunch food bc the hightea experience was not filling and left ALOT to be desired. Truly disappointing! Stay far away, spend your money elsewhere. People were all nice though
Matthew Cheung
Wonderful views, excellent mocktails and cocktails. The truffle fries are insanely good. Had a wonderful time.
How to reach Upstairs at The Gwen
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Why Upstairs at The Gwen may become Your Favorite Meetup Place for Catching Up, Celebrating or Just Hanging Out
Why rally at this place with your friends?
If you are looking for a destination that perfectly blends a vibrant urban energy with an intimate and relaxed ambiance, Upstairs at The Gwen is an exceptional choice. This rooftop venue, perched on the fifth floor of the luxury Gwen Hotel in Chicago’s Magnificent Mile, offers guests a unique escape amid the city’s hustle and bustle. Gathering here with friends means indulging in more than just food and drink; it’s about immersing yourself in an atmosphere that feels both exclusive and welcoming. The sophisticated rooftop setting offers panoramic views of Chicago's skyline, providing a stunning backdrop for lively conversations and memorable moments. Whether you want to toast over expertly crafted cocktails, share delectable small bites, or simply unwind while soaking in the scenery, Upstairs at The Gwen caters to the needs of groups looking for a stylish yet comfortable meetup spot. With a strong reputation for attentive service and a luxurious yet accessible vibe, it’s easy to see why this place garners a solid 4.0 rating from hundreds of reviews and why it’s ideal for socializing with friends or family.
What activities and experiences make Upstairs at The Gwen perfect for a group meetup?
Upstairs at The Gwen offers a range of experiences suited for group gatherings, combining dining, drinking, and socializing in a single impressive rooftop location. First and foremost, the venue’s all-day dining menu features a variety of dishes that are perfect for sharing. From starters like fresh burrata or flavorful dips and spreads to elegant yet approachable main courses, the food is designed to complement an engaged social environment. This focus on small bites encourages groups to order a variety of items, creating a communal dining experience that sparks conversation and connection. The culinary prowess behind the scenes, led by skilled chefs, ensures that each plate is not only visually appealing but also expertly balanced in flavors.
In addition to dining, the bar at Upstairs at The Gwen is a standout feature that greatly enhances group experiences. The mixologists craft innovative cocktails that go beyond the usual selections, offering guests creative and refreshing drink options. Friendly and knowledgeable bartenders make recommendations tailored to your group’s tastes, helping everyone find their perfect drink. This level of personalized service fosters a warm and engaging environment, making it easier for groups to relax and enjoy themselves. The presence of a lounge area alongside the restaurant encourages guests to move freely within the space, whether settling at dining tables or gathering around the bar for a more casual vibe.
How does the ambiance and location of Upstairs at The Gwen enhance group gatherings?
The unique atmosphere Upstairs at The Gwen strikes an exceptional balance between lively energy and soothing calm, making it an ideal setting for friend or family meetups. Its rooftop perch offers spectacular views of Chicago's iconic skyline, turning every moment spent here into a scenic experience. The open-air design lets guests enjoy fresh air while taking in city lights by night or basking in daylight by afternoon. This blend of an urban oasis creates a feeling of both excitement and escape, perfect for groups that want to celebrate an occasion or simply catch up in a peaceful yet chic setting.
Location-wise, being on Chicago’s famed Magnificent Mile means the venue is highly accessible via public transportation and close to many other attractions. This convenience allows groups to easily incorporate Upstairs at The Gwen into a larger day or evening out. Its placement within a luxury hotel adds to the prestige without making it feel intimidating, creating a welcoming space where groups can feel comfortable whether dressed up for a special night or enjoying a casual outing. The staff’s attentive service also plays a pivotal role in setting the tone; guests consistently report how team members anticipate needs and accommodate requests with warmth and professionalism. This attention to detail elevates the overall vibe and ensures that everyone in the group feels valued.
What kind of food and drink selections can groups enjoy?
Upstairs at The Gwen takes great care to offer a menu that caters to varied tastes within groups, ensuring everyone can find something appealing to share and savor. The culinary team focuses on quality ingredients and elegant flavors, with popular dishes like burrata and a range of light, flavorful appetizers that make for perfect starters or sharing plates. Reviewers consistently praise the delicious and beautifully presented food, noting that it perfectly complements the sophisticated atmosphere. The kitchen’s ability to blend creativity with comfort food classics makes it easy for groups to order diverse dishes and enjoy a series of tasting experiences together.
The bar and drink menu at Upstairs at The Gwen is equally impressive, from refreshing cocktails to a curated wine list that goes beyond the standard fare. The bartenders are known for crafting inventive cocktails tailored to individual preferences, helping each member of the group discover unique flavor profiles. Whether you’re in the mood for a smooth, spirit-forward drink or a lighter, fruitier option, the menu covers a broad spectrum of tastes. This versatility makes the place an excellent choice for groups with varied drinking preferences, ensuring there is something for everyone. The overall beverage experience complements the food perfectly, making each gathering feel thoughtfully curated.
Can Upstairs at The Gwen accommodate special events and how is the service?
Upstairs at The Gwen is well-suited for hosting special occasions, from casual meetups to celebrations like birthdays or small parties. The venue’s layout supports group dynamics well, offering spaces to mingle, dine, and relax without feeling cramped. Because it is on a rooftop, the ambiance naturally lends itself to memorable experiences, whether celebrating in the warm glow of a Chicago sunset or under the city lights after dark. Staff members are praised for their professionalism, attentiveness, and ability to personalize service, from quick drink recommendations to seating arrangements that fit the group’s preferences.
Groups also benefit from the venue’s flexibility and responsive team. Guests regularly note how staff respond promptly to requests and create a welcoming environment throughout the visit. This combination of efficient service and a stunning setting helps make any meetup at Upstairs at The Gwen exceptional and hassle-free. Whether you plan a quiet evening or a more lively gathering, you can count on the staff to contribute positively to the overall vibe and ensure your time together flows seamlessly. This reliable service adds an important layer of comfort and ease, key factors when choosing a place to reconnect with friends or family.
What makes Upstairs at The Gwen stand out among Chicago rooftop bars?
There are plenty of rooftop bars in Chicago, but Upstairs at The Gwen stands out for several important reasons. Besides the breathtaking city views and prime location on the Magnificent Mile, the venue offers a sophisticated yet relaxed atmosphere rarely found in competing rooftop spots. The balance between lively urban spirit and tranquil surroundings invites longer, more meaningful visits rather than just quick drinks. The fusion of exceptional cuisine, expertly crafted cocktails, and top-tier service creates a well-rounded experience that feels more elevated and thoughtful compared to typical rooftop bars.
Another distinguishing feature is its connection to the Gwen Hotel, a One Michelin Key rated establishment, which lends an air of refined luxury without the stiffness sometimes associated with high-end places. This connection translates into high standards in every aspect of the experience, from the quality of ingredients to the training of the staff. Guests can enjoy an upscale environment while still feeling at ease among friends. Additionally, the venue’s ability to accommodate both daytime and nighttime gatherings year-round — thanks to its layout and management — means it is versatile and reliable as a meetup spot. All these elements combine to make Upstairs at The Gwen a premier destination in Chicago for groups looking to enjoy great food, drinks, and views in a superb setting.