Rooftop season in Chicago, month by month
Chicago rooftops are not just a summer thing. What to expect on Fourteen from the first warm night in April to the igloos in January.
April and May: the first open nights
The first night above 60 degrees in April changes the mood of the whole city. We open the terrace doors on Fourteen as soon as the forecast allows, usually by mid-April, and switch the menu to lighter spritzes and gin drinks built on rhubarb and early herbs.
Evenings still cool quickly, so the fire tables stay on until Memorial Day. The sunsets are early enough that you can watch them before dinner, which makes late spring the best season for a relaxed drink without a reservation.
June to August: peak season
Summer on the roof is busy. Sunset moves past 8:20 pm, the terrace stays warm late into the night and there is music most evenings. Hotel guests can always walk in, but outside reservations for Friday and Saturday fill two weeks ahead.
Summer is also when Chicago throws its biggest outdoor events, from music festivals in Grant Park to the air and water show along the lakefront. From Fourteen you will not see the planes over the lake, but you will hear the city buzzing below you.
- Arrive before 6 pm on weekends for a seat on the terrace rail.
- The roof is 21 and over after 9 pm on Friday and Saturday.
- Order the Lake Effect. It is our most popular summer drink by a wide margin.
September and October: the locals' favorite
Ask any Chicagoan and they will tell you September is the best month in the city. The humidity breaks, the light turns gold and the skyline looks sharper. On the roof, we bring back whiskey and apple drinks and start our Midwest whiskey tastings.
October brings the harvest moon party, one of the few nights each year we sell tickets for the roof. Expect a DJ, fire tables, cider cocktails and a lot of people wearing their first sweater of the season.
November to March: the glass roof and igloos
Most Chicago rooftops close in November. Fourteen does not. We close the retractable glass panels over the main bar, light every fire table and set up six heated igloos on the terrace. Each igloo seats up to eight and can be booked for two hours with a minimum spend.
Winter drinks lean toward hot toddies, spiced rum and a smoked maple Old Fashioned. Snow on the terrace with the skyline lit behind it is one of the quietly beautiful sights in the city, and there is no line.
Planning a private event on the roof
If you want the roof to yourself, buyouts are possible on most weeknights and on some weekend afternoons. The space holds 180 standing, or you can take just the terrace for up to 60 guests.
Our events team handles music, food from Foundry, custom cocktails and even a signature drink named after the guest of honor. Reach out at least eight weeks ahead for summer dates.
