Chicagoans live for good rooftops or patios. Even year round, especially now. There are so many great rooftops and patios across the city, but I rounded out a few of my personal favorites that I have been to.
*Post updated November 2020* I added tents and heated patios.
I divided into two categories: upscale for your more date night or girls night out and chill, more the family friendly experience. I hope you like it!
Recently, we had a family brunch here on our last stop of the Open House Chicago Tour and it was delicious! The food, cocktails and the Lake Michigan views are stunning! There are two patios, I like the East facing one, it has heaters! I highly recommend the Purple Pisco drink pictured below.
Casati’s can be a date night spot or a place to bring the family! They are known for their pinsa pizza which is a low carb, super thin crust pizza. It’s delicious. We had their lasagna over Easter and it was some of the best I’ve had.
Their cocktail menu has also recently been revamped and they are good!
They now have domes for outdoor dining on their patio. You can reserve them for a $150 food and beverage minimum, seats 6 people. Great for a family night out celebrating something special.
Located in West Town on top of the brand new (opened in June 2020) Hyatt Hotel. We went for a date night here and I have to say the VIEWS are amazing. We tried a little bit of everything from the menu and some highlights were the mezcal margaritas, homemade beef empanadas (I would come here just for them) and the kale caesar salad.
They also cover part of it and it’s heated!
Joe’s Imports in the West Loop has now a patio you can make reservations at. Heated tents and outdoor dining is available.
I love their brunch menu and wine menu. I haven’t been back in months and would love to soon. The ricotta honey toast is SO GOOD! The patio is small, so reservations are needed in advance.
*Closed for the winter season*
We came here for our anniversary and loved it! Maybe one of the prettiest rooftops I have been on all year. The place is gorgeous and the food is even better. We loved the hibiscus margarita, sweet and sour eggplant with naan and the chicken thighs. They also took extra precautions due to COVID and everything was touchless, even the payment. They hand you a receipt, you scan and then paid! It’s also great because it’s a covered patio, which are harder to find.
Now tented areas with heaters, reservations with a deposit is needed.
I have actually never eaten here, but got drinks here when it first opened. And the views are amazing!! The space is right along with river and it’s stunning. I could probably hang out here for hours and just people watch.
OK maybe one of prettiest places in Chicago. They have tented their patio and are able to zip up the patio when it’s cold out!
The patio along the river is so cozy and gives me all the NYC vibes for some reason. I love it. The food is good, definitely enjoyed the scenery and drinks more. The appetizers were some of my favorite of everything I tried. I think overall it makes such great date night spot.
CURRENTLY CLOSED* May reopen later this season. is was the first stop for my 35th birthday and I loved it. The food is so good, the Wagyu Burger is insane! It’s on top of the Conrad hotel and has a great view overlooking buildings on Michigan Avenue. They also have have a spicy mezcal cocktail that is really great too.
*Currently closed as of October 30th
Since I mentioned my birthday, this was the second stop of the evening. I have always seen photos on Instagram, but can I just say, this rooftop and its views are STUNNING. It’s in the Peninsula Hotel, right off Michigan Avenue and you have such a close view of the Hancock building, it’s crazy. Ideal for a date night and a glass of wine will cost you at least $18 dollars per glass, so maybe not an all the time thing. Hahah
We got married here when it was the steakhouse Fulton’s on the River, so maybe I am bias, but the views of the river are beautiful!
They have a heated patio with a special menu here.
This newish hotel that just opened in West Loop is super trendy right now. There is a bar, pool and Stephanie Izzard’s, Cabra restaurant. I haven’t eaten here, but I did hang out on the rooftop for a bit. It’s got great views of the city, but it is rather small and gets crowded quickly.
Another West Loop gem, Aba is sister restaurant to Ema. This is one of my favorite places I ate at this year and they have a great patio with some perfect city views. I actually have never sat on their patio, but always have tried. Reservations are hard to come by. So definitely plan ahead. Read more about some of my other dining favorites this year here.
On the top of this hotel, this rooftop is one of my personal favorite views in the city. Architecturally, this whole building gives old school Chicago. The inside is nice, but the outside is the best part. I’ve always wanted to stay here too, hint, hint husband if you are reading 🙂
They have heaters available on their rooftop.
Located on the roof of Hotel Lincoln, stunning unobstructed views of Lake Michigan. They know have a retractable roof, so you can get those views year round. Tip- during the winter only, they do an awesome happy hour.
I’ve come here several times, but most recently with my blogger buddy and they have totally updated their outdoor patio. It’s super intimate, had a big fire place and perfect for a date night. I also saw they are now having movie nights, which is such a fun idea for a date! Very random, but they have really good heaters!
Located in Lincoln Square, they have some of the best farm to table food and their patio is so quaint and comfortable. It’s the best. I would definitely make reservations for a spot out there! Even if you can snag a seat outside, their brunch is delicious. (Pictured is their freshly squeezed blood orange mimosa).
They just recently updated their outdoor patio and it’s beautiful plus with heaters.
*closed for the season
Located on the Riverwalk, it’s kind of this hidden patio with fun drinks and boat rentals. There is lots of seating and space. I kind of felt like I wasn’t in Chicago for a little bit.
Love this place in Lincoln Park. They have lots of outdoor seating with a tented, heated patio that’s more family friendly. Then two outdoor patios that are 21 and over. Lot’s of space and fun decor to take pics for Insta. 🙂
I came here with some friends after an event and the outdoor seating is awesome. There are two patios with lots of space. I love the decor, it’s a super fun party atmosphere and lots of Instagram worthy shots. As for food, I think the appetizers like goat stix and jalapeno homies are the best on the menu.
I came here the night they opened and it’s super fun. It’s a 10,000 indoor/outdoor rooftop above Second City in Old Town. Board games, mini golf, bacce ball, tv’s, swings and more! We didn’t eat and had some cocktails, but the menu has tailgating type food like nachos (they look goooood), wings, etc. Plus, the view of downtown Chicago is incredible. A totally unobstructed view of the skyline! They plan on closing the rooftop and having winter games like curling once the weather gets cold.
Now they have two locations, Lincoln Park and Logan Square, it’s great for large groups and love their frozen negroni’s. Both locations have large patios with tables and big umbrellas. As for food, I always order the hush puppies.
We had a family dinner here last week and the patio was great! It’s very family friendly (early in the evening, we went at 4pm when they opened) and they are taking some great precautions for COVID. We all had our temperature checked, everything was sanitized in front of us and masks are encouraged, even when ordering at your table. We ordered the prosciutto and arugula pizza, very good!
You could also pick up food and head across the street to Lincoln Park for a picnic!
They have lots of fireplaces and heaters now, which makes it fall friendly. We went as a family and there is so much room, kids are welcomed. There are games for the adults, but kids can play too! There’s chalk, bubbles, bacci ball and more. Noah loved it! The patio is huge (like 6,000 square feet big) and you can probably find us here most of the summer. haha
This cafe and bar is located in West Town and has the coolest rooftop. They do have heaters now on the rooftop. Manny and I came here recently, but not eat here, although their brunch menu looks great. We had drinks on a Saturday around 3pm and very few people were on the rooftop. I highly recommend the cocktail The Primo. It’s made with a Greek liquor and it’s delicious!
One of my favorite places in the Riverwalk and getting wine at City Winery. They also have domes you can rent and reservations are required. Find more here.
We just had a family excursion on the riverwalk and it was so much fun! There are splash pads for the kids and Noah loved the boats go by. City Winery and Tiny Tap are great to grab a drink and people watch.
Located in Lincoln Park, their patio has a ton of seating, great for large groups. There is a large garage you can also reserve that is pretty isolated away from the rest of the crowd. They also have heaters as well and movie night on their patio.
Some you suggested patios like: Hampton Social, Warbler, Uncommon Ground, La Sud and more. You can check my highlights for more information, especially on winter outdoor dining options.
Until next time,