Odyssey Chicago River
The local cruise company, which has long offered dressy dinners on the lake, unveils a brand-new, glass-enclosed vessel for lunching along the river this summer (they’ll also offer brunch and cocktail hour cruises). Setting sail in July, the two-hour cruise includes a three-course meal and views for days. $57 and up, Chicago Riverwalk, 310 E. North Water; Odysseycruises.com
Wells St. Market
This coming-soon Loop destination melds the indoors and outdoors over 10,500 square feet. Ten vendors — including eateries like Pork & Mindy’s, Purple Pig offshoot Piggie Smalls and a brand-new sushi concept from Slurping Turtle’s Takashi Yagihashi — set up shop in the Studio K-designed interior; floor-to-ceiling windows open fully for an open-air experience, and a walk-up window and outdoor tables mean you never have to step inside. 205 W. Wacker; Wsmchicago.com
< West Lake Market
The Paramount Group, the culinary company behind Paramount Events catering, Eden restaurant and more, debuts an outdoor market happening the second Sunday of every month this summer (first up: June 10). Midwest vendors hawk their wares — think men’s shirts by Stock Mfg. (pictured), handmade ceramics by Grey Remedy and skin care products from Scratch Goods. 10 a.m.-2 p.m. 1748 W. Lake; Westlakemarket.org
1-3 Do Division Street Fest | Division between Damen and Leavitt
1-3 Lincoln Park Greek Fest | St. George Greek Orthodox Church, 2701 N. Sheffield Don’t miss: New this year, a craft fair comes to the cultural fest.
8-10 Ribfest | Lincoln, Irving Park and Damen
8-10 Chicago Blues Festival | Millennium Park, 201 E. Randolph
9-10 Printer’s Row Lit Fest | Dearborn between Polk and Harrison Don’t miss: Author Joyce Carol Oates and chefs Rick Bayless and Sarah Grueneberg make appearances.
9-10 Old Town Art Fair | 1763 N. North Park
9-10 Pilsen Food Truck Social | 18th from Racine to Throop Pro tip: Opt for a sampler ticket ($20) to try six mini portions from trucks like 5411 Empanadas, Carnivale and Da Lobsta.
15-17 Taste of Randolph | 900 W. Randolph
16-17 Chicago Pride Fest | Halsted from Addison to Grace Don’t miss: A fashion show, drag show and Mya’s headlining performance are just a few of the colorful events lined up.
11-15 Taste of Chicago | Grant Park, 337 E. Randolph Pro tip: Check the schedule before you go: Pop-up restaurants like Brightwok Kitchen, Broken English and Mad Social are available for just a day or two.
13-15 Windy City Smokeout | 560 W. Grand Don’t miss: Former Splash cover star Brett Eldredge headlines on Saturday.
13-15 Square Roots Festival | Lincoln between Montrose and Wilson
14-15 Roscoe Village Burger Fest | 2000 W. Belmont
15 Chinatown Summer Fair | 2200 S. Wentworth
20-22 Pitchfork Music Festival | Union Park, 1501 W. Randolph Don’t miss: Ms. Lauryn Hill will perform songs from her album “The Miseducation of Lauryn Hill,” which turns 20 this year.
2-5 Lollapalooza | Grant Park, 337 E. Randolph Don’t miss: Headliners include the Arctic Monkeys, Bruno Mars, Odesza, Post Malone, Travis Scott and The Weeknd.
18-19 Air & Water Show | North Avenue Beach, 1600 N. Lake Shore
30-Sept. 2 Chicago Jazz Fest | Millennium Park, 201 E. Randolph
31-Sept. 2 North Coast Music Festival | Union Park, 1501 W. Randolph
Navy Pier Flyover
The super-congested section of the Lakefront Trail near Navy Pier — from the river bridge to Jane Addams Park — is finally being streamlined in three phrases. The path is open (though limited) in the meantime; if you bike past, stop and check out artist Chakaia Booker’s larger-than-life textural sculptures.
312 River Run
Three years ago, Chicago got The 606; in 2019, it will get this new trail, connecting the Albany Park, Avondale, Irving Park and North Center neighborhoods. Construction began last fall and, when completed, the path will include the city’s longest pedestrian bridge over the Chicago River, spanning 1,000 feet long and 16 feet wide.
With more than 200 seats on its rooftop patio in Fulton Market, Lettuce Entertain You’s Aba is the place to be this summer. Sister spot to Chef CJ Jacobson’s Ēma (which means “mother” in Hebrew to Aba’s “father”), Aba will continue the Mediterannean theme with dishes like hummus with seabass ragu, skirt steak with harissa jus, mezze, veggies and more. 302 N. Green; Abarestaurantchicago.com
The upscale River North sports bar moves outside with the addition of a new 150-seat rooftop this summer. With a vintage concession stand bar, upholstered bleacher-style seating and sports memorabilia on display — plus TVs — it’s the next closest thing to being at the game. 324 W. Chicago; Bouncesportingclub.com
Chef Christine McCabe has been selling sandwiches and salads from a walk-up window on Armitage for years; this spring, though, she transformed the operation into a full-scale restaurant along the North Branch of the Chicago River in Lincoln Park. The patio currently seats 30, and the nautical theme will be especially apt when the boat-up dock is completed later this summer. 1438 W. Cortland; Interurbanchicago.com
Beatnik on the River
The highly Instagrammed West Town spot gets an outdoor outpost downtown this year. Serving global cuisine and refreshing cocktails — including a slushie option or two — the new location has everything you love about the original, plus a sweet view. 180 N. Wacker; Beatnikontheriver.com