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Memorial Day Checklist

Memorial Day weekend marks the start of Chicago’s summer season, so make the most of it and check out these fun outdoor (Yes, a rooftop bar counts!) destinations. Whether it be luxe terrace lounging or soaking up some Vitamin D at a private cabana, you’ll be starting summer off on the right foot.

Roof on theWit celebrates five years with a bevy of Memorial Day weekend activities.

1. The Terrace at Trump
Our go-to rooftop lounge and restaurant is back with additional seating, a fresh Mediterranean-inspired menu and a new list of cocktails that are only available after sunset. The coolest part? These drinks, which are inspired by the four elements, are served in handmade ice sculptures. Cheers! 401 N. Wabash Ave., 312.588.8600

2. Castaways Bar and Grill
Reopening for the season on May 24, Castaways on North Avenue Beach is celebrating with live entertainment and their popular frozen cocktails. Our advice? Round up a few friends and reserve one of the two private cabanas for the ultimate Memorial Day weekend experience. 1603 N. Lake Shore Drive,

3. Roof on theWit
We know it’s hard to believe, but Roof on theWit turns five years old this month, and the perennially packed lounge is marking the occasion with a weekend lineup of top DJs and the return of the popular Roof Sundays party May 25. New this year is Roof Mondays, a 15-week movie screening event that debuts on Memorial Day with The Hangover. 201 N. State St., 312.467.0200

4. The Second City’s Neighborhood Tour
For those looking to learn a bit about Chicago’s history (sans the sometimes inescapable yawn), join The Second City for its walking tour combining humor with informative tidbits about Old Town, Second City alumni haunts and the off-the-wall stories that come with them. Sundays at 10:30AM and Wednesdays at 4PM. Tickets $15. 1616 N. Wells St., 312.337.3992

5. Randolph Street Market
Marking its summer debut May 24-25, the acclaimed indoor-outdoor Chicago market is back with more than 250 vendors offering everything from rare antiques to vintage fashion (and everything in-between). On top of the fabulous finds for your home, expect delicious food, cocktails and live music. 10AM-5PM. Tickets from $8. 1340 W. Washington Blvd., 312.666.1200