By Emmy Conway

The Bean at Chicago's Millenium Park. Credit: David Paul Ohmer.
The Bean at Chicago's Millenium Park. Credit: David Paul Ohmer.

There’s something about a cold Chicago winter that makes the locals cherish summertime in the city. Come May, we crack open our windows for the first time in months and emerge from hibernation in anticipation of all that Chicago has to offer: the lush green parks, the miles of lakefront beaches, the beautifully manicured Mag Mile. Come summer, Chicago vacations take front and center for incredible big city fun, with numerous outdoor festivals, concerts, and parades all season long. If you can believe it, there are over 400 in total from May through September! And, as a long-time resident of this fair city and an avid festival attendee, I give to you my top picks.

Blackstone Hotel
Blackstone Hotel

Blues Festival, June 11-13:  If you’re going to go to a Blues Fest anywhere, it should be in Chicago. This weekend celebration features top Blues artists from around the world right here in the home of the blues. Get a good night’s rest at the newly restored Blackstone Hotel, an historic Chicago hotel steps from the fest.  And, be sure not to miss a meal at Chicago’s new gastronomic hot-spot, Mercat a la Planxa, on the ground floor of the Blackstone.  It’s popular for a reason… the food is out of this world.  So, make a reservation.
Insider tip: Bring a blanket to the festival, preferably a water resistant one.  You’ll be sitting on the lawn for a while and knowing Chicago weather, it could be slightly wet.

Pool at the Essex Inn
Pool at the Essex Inn

Taste Of Chicago, June 25 – July 4: Local restaurants serve up their signature dishes at this popular festival. Beside tasting fare from all corners of Chicago, you can enjoy live music all day long at one of The Taste’s two stages. The food is hot, but the weather can be hotter. And when Chicago vacations heat up, it’s time for a dip at one of Chicago’s few downtown pools located in the Essex Inn. This family-friendly hotel across the street from the festival was recently renovated and can come with a nice price tag.
Insider tip: Visit the Taste on a weekday and you’ll be less likely to have your Rainbow Cone bumped out of your hands. Also, enjoy Chicago’s July 4th fireworks from the peninsula at the Adler Planetarium to avoid crowds at Navy Pier.

Hard Rock Hotel Chicago
Hard Rock Hotel Chicago

Pitchfork Music Festival, July 16-18: Somewhere in the depths of your closet is that green plaid flannel from ’94. Pack it up and head over to the nation’s hippest music festival, Pitchfork. You’ll hear the globe’s newest, most progressive bands and you’ll grow your indie-cred to boot. Cool off after the shows with a PBR at Gold Star or Rainbow, two Wicker Park bars with an indie scene reputation. Then rest your ears for the night at the budget-friendly Congress Plaza Hotel, an “El” ride away from the festival. Or, you can live like a rock star for a night at Hard Rock Hotel Chicago. This musically infused hotel even includes complimentary Gibson guitar rentals. Rock on!
Insider tip: If you only have one day, check the Pitchfork lineup and buy a one-day pass. Book your summer stay at the Hard Rock Hotel now and you can also enjoy up to 25% off.

Swissotel Chicago
Swissotel Chicago

Chicago Air & Water Show, August 14-15: Pull out those dusty binoculars and a battery-powered radio and head over to The Chicago Air and Water Show. For one weekend in August, two million people ascend upon Lake Michigan‘s shores to witness nautical and aerial feats of grandeur. Enjoy the finest of Chicago vacations by scoring a bird’s eye view of the show from a room on one of Swissotel Chicago’s 42 lakefront floors. Then, soar downstairs to enjoy dinner at The Palm, home of the most delicious bone-in rib eye I’ve ever had the pleasure to eat.
Insider tip: Pack a picnic and perch on the west side of Lake Shore Drive opposite North Avenue Beach. You’ll avoid the crowds and still have great views of the jet formations above.

Oktoberfest, September 24-26: Set in what was historically Chicago’s German neighborhood (and home to yours truly), Lincoln Square’s Octoberfest is a beer-drinking, Knackwurst-eating, lederhosen-wearing celebration! Join my family and me at this kid friendly neighborhood festival. For a taste of German culture year-round, Lincoln Square is still a great bet. Head on over to the Brauhaus for a fun-filled evening complete with an Oompa Band and its famous 2 liter beer “boot.” For an authentic German dining and drinking experience, head south to my favorite place, Laschett’s Inn on Irving Park Rd.  You just can’t beat the rouladen (or the free shot of schnapps at the end of the meal).
Insider tip: If you’re staying downtown, jump on the El’s Brown Line headed north and get off on at the Western stop.  The festival is located in the train station’s parking lot.

Sweet deals in the Windy City
Book your trip to Chicago now and you can take advantage of two sweet summer deals: our Summer Hotel Sale with free nights and savings of up to 40% off, and big savings on local activities and events, including 15% off Spirit of Chicago Dinner Cruises and 30% off  Go Chicago Cards.

A native Chicagoan and Senior Market Manager for Orbitz Worldwide, Emmy Conway is a travel professional with over a decade of experience. When this Chicago mom isn’t running after her one-year old, she enjoys strolling about her “kind of town.”

Tagged: Chicago Vacation, Holidays & Events, Hotels, Orbitz Travel Insider, Travel Tips

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