1510 N. Wells St. 312-649-9640
With its oversized booths for groups and a TV screen so big it nearly covers an entire wall, the main floor of this Old Town sports bar has plenty to offer. But on a warm afternoon, you can't beat a seat on the second floor, where a retractable greenhouse ceiling opens to let in the fresh air and sunshine.
The J. Parker
1816 N. Clark St. 312-254-4747
Thanks to the sweeping vistas of the lakefront, downtown skyline and Lincoln Park from this 13th floor rooftop lounge at Hotel Lincoln, you'll come for the photo ops and stay for the refreshing craft cocktails. Chef Paul Virant—of award-winning restaurant Perennial Virant, located just downstairs—presides over a menu of seasonal snacks.
160 E. Pearson St. 312-573-5160
You'll have to cross The Ritz-Carlton's lobby, take the elevator and walk through Deca restaurant to arrive at this outdoor lounge. Thankfully, the journey from street level ends at a terrace tastefully decorated with elegant wicker furniture, a wave-shaped glass wall and a silver sculpture called The Lenz. Polished servers float by with trays of cocktails bound for the welldressed clients you'd expect at The Ritz.
1501 N. Dayton St. 773-244-1234
This neighborhood sports bar is just a few blocks' walk from the nexus of North Avenue, Clybourn and Halsted in the Weed Street District. The second-floor rooftop, called The Upper Deck, features pillow-strewn couches, ottomans and plenty of TVs for a comfy game-watching scene.
940 W. Weed St. 312-337-3486
After standing in line to have your ID checked alongside sports fans or country music concert ticket holders (depending on the night), bypass the main door and head up the outdoor staircase to get to Joe's rooftop deck. A covered bar provides shade and shelter from surprise rain showers.
800 N. Michigan Ave. 312-239-4030
At this picturesque terrace on the seventh floor of the Park Hyatt, leafy planters, umbrellas and bud vases on each table help the space live up to the name. While the Park Hyatt's indoor restaurant Nomi Kitchen features stunning views to the east, the terrace looks south and west toward the towering buildings of River North and the Gold Coast.