Flickr/marksperfectpics
Caffè Oliva
Bridge House Tavern
Japonais by Morimoto
Flickr/lobstar
Quay
The Dock at Montrose Beach
River Roast
Oak Street Beach
O'Briens Restaurant
Flickr/hubster
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1. ESTATE Ultra Bar 1177 N Elston Ave, Chicago, IL 60642 (West Town)

Claiming to be Chicago’s biggest al fresco rooftop, ESTATE Ultra Bar is the ideal Noble Square destination for those looking to sip with a scenic view and trendy ambience. While food is available in the way of New American light fare, the focus here is on the drinks, as the bar slings cocktails with “skinny” variations for the health-conscious and craft brews for the bros who throw down. If you’re unwilling to peel your eyes from the sweeping views of the Chicago River, there’s bottle service to boot.

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2. Castaways Bar & Grill 1603 N Lake Shore Dr, Chicago, IL 60614 (Lincoln Park)

Located at North Avenue Beach, this bar and grill serves american classics (think burgers and sandwiches) along with a full menu of island worthy umbrella drinks, from daiquiris to margaritas. In addition to incredible lake views, this bar-on-a-boat has South-Beach style cabanas you can rent out to privately sip your very tropical drinks. Of course, this place is a hot spot during the summer, so come early to grab a good spot to take in the sun and sand.

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3. Caffe Oliva 550 E Grand Ave, Chicago, IL 60611 (Magnificent Mile)

On the low-key Ohio Street Beach sits this low-key beach bar, serving Mediterranean inspired food like Greek bruschetta, flat-bread pizzas, and souvlaki. The cocktail menu covers all the summer favorites and then some, plus a decent list of beers and wines.

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4. Waterfront Café 6219 N Sheridan Rd, Chicago, IL 60660 (Edgewater)

This super-chill spot is one of the city's best kept secrets. It's great for kicking back with a Cuba Libre and listening to live music. The craft beers and caipirinhas don’t make for a bad afternoon outing either.

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5. North Pond 2610 N Cannon Dr, Chicago, IL 60614 (Lincoln Park)

When it comes to romantic restaurants in Chicago, few top North Pond, a waterfront hideaway within Lincoln Park. Chef Bruce Sherman sources seasonal ingredients from local markets and farmers to craft his menu, which is split between a tasting dinner with optional wine pairings and Ă  la carte items. The Arts and Crafts-style building, originally built in 1912 for ice skaters, is as picturesque as the park surroundings.

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6. Bridge House Tavern 321 N Clark St, Chicago, IL 60654 (River North)

Set in the former Flatwater Grill space, BHT is a modern gastropub that features a two-tiered, riverside terrace. Though you invariably come to Bridge House Tavern for the waterfront ambience, the food is on par with similar upscale American comfort spots that serve a variety of land and sea offerings.

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7. Japonais by Morimoto 600 W Chicago Ave, Chicago, IL 60654

Surpass the loud dining hall and head downstairs to The Blue Room, which offers a unique view of Chicago -- the river is literally level with you, and on the other side of it? The more industrial side of Chicago. Ask for sake recommendations and settle in with some next-level seafood creations.

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8. Chicago Cut Steakhouse 300 N LaSalle, Chicago, IL 60654 (River North)

A steakhouse hit among the power meal set, Chicago Cut attributes its quality cuts to the Colorado cattle it raises 1,300ft above sea level. The beef is dry-aged for 35 days then butchered on-site, and no matter what you order (the bone-in prime rib is knockout good), expect dense muscle and an intense flavor. The 225-seat space, outfitted with red velvet booths, overlooks the river.

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9. Smith & Wollensky 318 N State St, Chicago, IL 60611

If you prefer your steaks dry-aged and butchered on site and a your wine lists lengthy, and if you prefer enjoying those steaks and wines with a scenic view of Chicago while you sit along the water in Marina City, you might want to hit up this classic.

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10. Quay 465 E Illinois St, Chicago, IL 60611 (Streeterville)

Setting up shop in the former DeLaCosta space, this sprawling resto-lounge boasts boat access via a riverside docking area, but no matter your vessel you can sail away to snackage like crispy-parsley-topped bacalao fritters, pork rillettes w/ pickled okra, shrimp-toast-sided sirloin, and a veal chop w/ potato croquettes, pearl onions, and minted peas, a welcome departure from their traditional pairing: urinal cakes.

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11. The Dock at Montrose 200 W Montrose Harbor Dr, Chicago, IL 60640 (Uptown)

A huge bar menu, live music almost every night, and unique eats make this one of the coolest spots in Chicago summers. If your into reggae, or want to pretend that your in the islands and not just off work, check out Reggae Wednesdays.

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12. River Roast 315 N LaSalle St, Chicago, IL 60654 (River North)

On the north bank of the Chicago River is River Roast, an upscale tavern that combines traditional British roasts with new American ingredients. The menu revolves around roasted proteins -- fish, beef, chicken, pork -- that are carved table-side for two. There are also a variety of small plates and vegetables to share. The large space includes two bars and an expansive riverside patio.

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13. Oak Street Beach Food + Drink 1001 N Lake Shore Dr, Chicago, IL 60611 (Magnificent Mile)

Mixing it up between chill nights of cornhole and more lively DJ nights, this bar sticks mostly to classic drinks and simple beach bar food, but it's all top quality.

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14. South Branch Tavern & Grille 100 S Wacker Dr, Chicago, IL 60606 (South Loop)

This upscale and modern spot offers a huge craft beer list and seasonal cocktails on their cozy, riverside patio.

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15. Rivers 30 S Wacker Dr, Chicago, IL 60606 (River North)

This place calls itself a “Euro-American Bistro,” and serves Metropolitan Flywheel riverside so you can soak up the sun and booze all in one lunch break.

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16. O'Briens Riverwalk Cafe 45 E Riverwalk S, Chicago, IL 60601 (Near North Side)

With a name like O'Brien's, the menu featuring Irish pub favorites isn't much of a suprise. Pair that with the stiff drinks and killer river & skyline views and you have a great summer spot.

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18. Galileo's 1300 S Lake Shore Dr, Chicago, IL 60605

Galileo's, the Adler Planetarium’s in-house cafe, is an often overlooked spot that is perfect waterfront boozing. Plus, planets and stuff.

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19. Patio at Cafe Brauer The Patio At Cafe Brauer, Chicago, IL 60614 (Lincoln Park)

Located in a serene setting at the edge of Lincoln Park’s South Pond on the outskirts of Lincoln Park Zoo, this romantic Tavern on the Green-style restaurant only serves food to the public during the summer when their lagoon-side outdoor patio is open. The rest of the time you’ll need to rest it out for a wedding or private event.

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20. Riva 700 E Grand Ave, Chicago, IL 60611 (Streeterville)

This Navy Pier gem serves excellent seafood complemented by great views of Lake Michigan and downtown Chicago. The menu dedicates an entire section to crab and lobster plates, like a house lobster and linguine entree. There are house seafood specialities and appetizers, and if you don't like fish, fear not because there are plenty of steaks and chops.