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How to Wander Chicago Rooftops like an Insider.

My favorite place to be when I’m at home is on the patio.  So, what’s better than a balcony or patio while traveling?  A rooftop with scenic views and good drinks/eats.  Chicago serves up rooftop pleasures in style.  There’s an array of rooftops offered by restaurants and hotels, wander to 3 of them with me.  I’ll tell you how to make a rooftop experience part of your sightseeing adventure in Chicago.

I’m a native Chicagoan with a deep love for Chicago’s skyline, lakefront, and food culture.  Going back almost a decade later proved only one thing, that everything gets better with age.  The lakefront seemed prettier with some of the bluest hues in Lake Michigan that I ever recalled seeing.  The skyline had new buildings and the bright lights of the city shimmered in sexy vibes.  This place will seduce you into staying up all night and spending all your money.  But you will enjoy it.

The first thing you should know about making plans in Chicago is that you indeed need to make plans.  Well ahead of time.  This is even more important if you plan on doing something during the weekend or a holiday.  Chicago is a “make a reservation” city.  This can be true for clubs, restaurants, rooftop bars, and during this pandemic, even Lincoln Park Zoo (one of the country’s few free zoo’s) requires a reservation.

chicago pin this

If traveling to Chicago during this time, be advised of changing travel warnings:
Emergency Travel Order
Updated 5/4/2021
Based on data as of 5/3/2021

In response to the changing dynamics of COVID-19 transmission across the United States, and to support Chicago’s efforts to contain the spread of COVID-19, the City is issuing a Travel Order applicable to anyone coming into the City of Chicago from designated states with a significant degree of community-wide spread of COVID-19. Anyone traveling from a state on the Orange list is directed to obtain a negative COVID-19 test result no more than 72 hours prior to arrival in Chicago or quarantine for a 10-day period (or the duration of their time in Chicago, whichever is shorter). The Order is subject to the limited exemptions outlined in the ‘Exemptions tab’.

Making Reservations

Most of the restaurants and rooftop bars that you may want to visit can be found on either Open Table or Tock.

Not all reservations are created equally and just like a car, your mileage may vary.  Some places have strict seating rules and will not allow more than a party of 4, nor will they allow you to reserve 2 groups at the same time.  I could only book 1 group of 4 at one place while another let me book up to 10.  Some require deposits.  Read carefully, plan accordingly, and enjoy!

***TIP – Every place that we went to hands or shows you a QR code which you use to access the menu.  If you have not gotten comfortable with modern contactless conveniences, now’s a good time to start.*** 

On a Friday or Saturday night, expect live events, DJ’s, or more of a club experience at some venues.  Most automatically add a 20% gratuity as well.  If you’re planning on a late night, keep in mind that the kitchens typically close by 10PM so you won’t be able to continue ordering food, just drinks.

Just a Reminder…

You’ll find a lot of links to various resources on this site, some of these links are affiliate links that pay me a commission at no extra cost to you. If you make a purchase through these companies, this supports the photos and tips that are provided to inspire you in your own travels.

1.   LondonHouse Rooftop

85 East Wacker Drive, Chicago, IL 60601

Panoramic views of the city from the 21st and 22nd floor. Enjoy classic cocktails and imaginative American cuisine indoors or outside. Book online for London House rooftop reservations of 2 – 6.

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TripAdvisor
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 (Reserve on Tock)

2.   Upstairs at the Gwen  – 5th floor

521 N Rush St 5th Floor, Chicago, IL 60611

Easy to book with a beautiful setting. The firepit table seats up to 6 and requires a $75 deposit with reservation.  There’s a little bit of heat to be gained from it but if it’s chilly, that won’t keep you warm.  This has such a nice chill vibe that you could get pretty comfortable and let the night slip away.  No deposit is required for the other types of seating indoors or outdoors.

FROM THE MENU:

JUNGLE BIRD $14
jamaican rum, campari, pineapple, lime, demerara syrup
FRIDA’S GARDEN  $15
black pepper infused blanco tequila, lime, manzanilla syrup, strawberry

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(Reserve on Open Table)

3.   Cerise – 26th floor

203 N Wabash Ave 26th floor, Chicago, IL 60601

Another easy one to book with a beautifully interesting setting.  If you’re familiar with Virgin Hotels, then you know to expect a little of the unexpected.  From the red lips seat that I should’ve photographed at the front door to the disco ball by the entrance and the swings on the outdoor patio area, there is something for your eyes to behold in every direction.  While the music wasn’t especially moving, this one had the absolute BEST service hands down.  Our server was awesome, friendly, and fun.  I don’t know if it’s the eclectic flare, the friendly service, or the totally unpretentious vibe but I would return.  As a matter of fact, I am looking forward to it.

FROM THE MENU:

Grilled Octopus
$17.00
fines herbs lemon salad, shaved shallots, gochujang aioli
 
Purple Reign
$15.00
hendrick’s gin, lavender syrup, teapot bitters, fever tree tonic, cucumber, lemon

Summer Love Sangria
$15.00
rosé, grapefruit new amsterdam vodka, grapefruit, lemon, lime

VRBO

4.   Raised (Reserve on Tock)

1 W Wacker Dr, Chicago, IL 60601

I eventually cancelled my reservation for Raised due to scheduling conflicts but would’ve really enjoyed the unique view of the Chicago River, Marina City, and the Michigan Avenue Bridge.  This one is popular and was hard to re-schedule as there was no availability left for the weekend by Thursday.

5.   Offshore (Reserve on Tock)

1000 E Grand Ave, Chicago, IL 60611

I’ve always enjoyed Navy Pier, so this seemed like a great way to soak up the views of the city.  On a chilly night with the lake breeze, the firepits might come in handy.  Sadly, I booked for 4 ahead of time and then forgot to have someone else book another table.  The next day, everything was sold out.  We skipped it but we’re saving it for next time, you really do have to check out the world’s largest rooftop bar.

6.   Roof on theWit – 27th floor (Reserve on Open Table)

201 N State St 27th Floor, Chicago, IL 60601

This was another one I had to cancel when I jumped at the chance to have my sunset at LondonHouse.  In retrospect, I wish I had kept this reservation instead.  Honestly, I would’ve liked to experience every single one of the dozens of rooftops in Chicago for each of their own unique skyline views and menus.What’s the #1 hotel in Chicago? Read reviews & find hotel deals on TripAdvisor!

How to Save $$$ – Happy Hour Rooftop Specials 

(Always call to verify as changes can occur quickly.)

  • Cerise – Every Thursday from 5 – 9PM.
  • LondonHouse Rooftop – Monday to Thursday 4 – 7PM $10 house champagne and discounted snacks.
  • Upstairs at the Gwen – Monday to Thurdays 4 – 5:30PM – $10 cocktails, $8 house wine, $5 fries + more.
  • Roof on theWit – “Wind Down Weekdays” Monday through Friday 4-7 p.m. $10 Dealer’s Choice cocktail, Roof Macaron Flight $10, full menu.
  • I|O Godfrey Hotel Rooftop – Monday through Friday 2 – 5PM  – $8 Frose All Day, $7 house Rose, $6 Black Truffle Fries, full menu.

This is only a sampling of the rooftops that await you in Chicago.  Whether you decide to party on the weekend or save with a happy hour toast, you’ll enjoy good times with good views wherever you go. 

mich ave tulips

Michigan Avenue Tulips

Extra Fun Fact

Every October and November, thousands of tulip bulbs are planted in the Michigan Avenue planters along the 2 mile stretch from Roosevelt Road to the end of the Magnificent Mile at Oak Street.  They are protected and cared for, to ensure that Spring blooms of tulips fill the planters the next year.  Just before Memorial Day, the summer displays are planted.  Early May is a great time to see the Spring tulips in full action.

Happy Wandering on the Rooftops in Chicago.

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