Al Fresco in Chicago


With warmer weather and longer days comes more opportunities for rooftop and outdoor dining destinations! Whether you’re planning a night out with friends or a perfect date-night, there are so many hot spots waiting for you to explore. 


Opening back up in late April, you certainly do not want to miss out on the world’s largest rooftop deck! With surrounding spectacular views of the Chicago skyline and Lake Michigan, as well as fun and Instagrammable drinks, you definitely will not leave here without plenty of pictures to share and look back at. 

Kennedy Rooftop 

This first come, first served rooftop is only open Thursday to Sunday at specific times, and trust us, you want to be there one of these days. Whether for the specialty drinks and delicious dishes, the iconic views of the complete city skyline from the John Hancock to the Willis Tower, or both, this hotspot will always be ready to make your day a little brighter!

Geja’s Cafe 

If you’re looking for a new date destination, Geja’s is an excellent choice for you! With a nickname like “Restaurant of Romance,” you can be sure that this night will wow anyone who has your heart. They even have new pergolas on the outside patio that are ready for you to break in as you share delicious fondue in the open air! 

Replay Lincoln Park 

Calling all The Office lovers, Replay’s Back to The Office pop-up is open from now until May 16th! Every inch of space, including the outdoor patio, will be transformed into iconic spots inspired by the show so you can celebrate with your favorite coworkers at “Dunder Mifflin.” Try the Michael Scott-inspired cocktails and any item on the themed food menu to make the experience even more exciting!

 Thorn Restaurant & Lounge

This closest off-airport hotel to O’Hare features breakfast, lunch and dinner as well as brunch and late-night cocktails. The menu includes comfort food favorites, signature Rose items, and Chef’s daily specials that will surely leave you feeling satisfied. For Mother’s Day, Thorn will also be offering a High Tea on Sunday, May 9 with two seating’s available at 11 a.m., and 2 p.m. This includes complimentary parking, live music from Dina Bach, and a curated menu to set the scene of an elevated high tea! Indoor and outdoor seating are available for whatever guest prefer.  

Water’s Edge  

If you’re looking to venture outside of the city limits for a day, this upscale Oakbrook café offers fresh salads, classic sandwiches, soups and entrees for both breakfast and lunch. Guests can choose between a setting of intimate and cozy in the Hearth Lounge or relaxing on the serene patio with views of the property’s private lakes and pristine landscaping. No matter where you choose, the experience will be like no other. 

Fulton Market Kitchen 

Try the brand new menu as you choose between either outdoor or indoor dining at this part restaurant, part art gallery crossover! There are plenty of 4-Star Rated Chef Harootunian’s seasonal menu items and locally-sourced cocktails to taste. With a limited schedule of Thursday through Sunday, a reservation may be necessary to sec ure your spot!


Get a taste of Sicily at this South Loop authentic Italian eatery that offers a wide range of classically-inspired antipasti, pizza, salads, seafood, fresh pastas and more. Pair any dish with a beverage from the full bar indoors or pull up a seat under the outdoor pergola for an amazing outdoor dining experience you can’t beat! 


Soak up the sun at the perfect urban atmosphere for both Chicago residents and tourists alike to enjoy. Their amazing outdoor area features fire pits, cabanas, couches and an outdoor bar to satisfy your every desire! On the menu, you can find an array of flatbreads, appetizers, and salads to go with any of the variety of specialty-crafted cocktails, craft beers, draft beers, or wine.

Written By: Natalie Kokaska

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