Chicago Trip 2026
Items in this hypelist
Places
Chicago River Boat Architecture Tours
Streeterville, Chicago · Chicago River Boat Architecture Tours · 465 N McClurg Ct, Chicago, IL 60611, USA
Shedd Aquarium
Near South Side, Chicago · Shedd Aquarium · 1200 S DuSable Lake Shore Dr, Chicago, IL 60605, USA
State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.
Chicago Cultural Center
Chicago Loop, Chicago · Chicago Cultural Center · 78 E Washington St, Chicago, IL 60602, USA
Free art & shows in an 1897 Beaux-Arts building with vaulted lobby, mosaics & 2 stained-glass domes.
Art Institute of Chicago
Chicago Loop, Chicago · Art Institute of Chicago · 111 S Michigan Ave, Chicago, IL 60603, USA
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
Chicago Riverwalk
Chicago Loop, Chicago · Chicago Riverwalk · Chicago, IL 60601, USA
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
Chicago Bean
Chicago Loop, Chicago · Cloud Gate · 201 E Randolph St, Chicago, IL 60602, USA
Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.
WNDR Museum
West Loop, Chicago · WNDR Museum · 1130 W Monroe St, Chicago, IL 60607, USA
Multi-sensory, contemporary installations by artists including Yayoi Kusama.
The Strip Club Photobooth Studio
West Town, Chicago · The Strip Club Photobooth Studio · 1702 N Damen Ave, Chicago, IL 60647, USA
Lincoln Park Zoo
Lincoln Park, Chicago · Lincoln Park Zoo · Chicago, IL 60614, USA
Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.
Freehand Chicago
River North, Chicago · Freehand Chicago · 19 E Ohio St, Chicago, IL 60611, USA
Bohemian-chic hostel in a vintage building featuring a bar, a cafe & continental breakfast.
Adler Planetarium
Near South Side, Chicago · Adler Planetarium · 1300 S DuSable Lake Shore Dr, Chicago, IL 60605, USA
Interactive exhibits & high-tech sky shows entertain stargazers, lakefront views are a bonus.
Skydeck Chicago
Chicago Loop, Chicago · Skydeck Chicago · 233 S Wacker Dr, Chicago, IL 60606, USA
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
360 CHICAGO
Streeterville, Chicago · 360 CHICAGO · 875 N Michigan Ave 94th floor, Chicago, IL 60611, USA
Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.
Navy Pier Fireworks
Streeterville, Chicago · Navy Pier · 600 E Grand Ave, Chicago, IL 60611, USA
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
Restaurants
DJ's Great Room
Near North, Chicago · DJ's Great Room · 908 N Wells St, Chicago, IL 60610, USA
Doc B's Restaurant (Gold Coast)
Streeterville, Chicago · Doc B's Restaurant (Gold Coast) · 100 E Walton St, Chicago, IL 60611, USA
Small-chain American spot offering seasonal comfort food in stylish, contemporary surroundings.
Joy Yee Plus
Armour Square, Chicago · Joy Yee Plus · 2159 S China Pl, Chicago, IL 60616, USA
Local spot serving a host of Pan-Asian eats ranging from Japanese hot pots to Vietnamese sandwiches.
Giordano's
Illinois, Oak Park · Giordano's · 1115 Chicago Ave, Oak Park, IL 60302, USA
Known for deep-dish pizza, this casual chain serves other classic Italian food, plus beer & wine.
Il Porcellino
River North, Chicago · Il Porcellino · 59 W Hubbard St #2, Chicago, IL 60654, USA
Casual-chic, vibrant spot for housemade pastas, Italian specials, and wine.
Gilt Bar
River North, Chicago · Gilt Bar · 230 W Kinzie St, Chicago, IL 60654, USA
Lounge with vintage library decor serving the same upscale American menu as Gilt Bar upstairs.
Daisies
Logan Square, Chicago · Daisies · 2375 N Milwaukee Ave, Chicago, IL 60647, USA
Stylish spot with seasonal pasta and vegetables on the New American menu, along with craft cocktails.
Cindy's Rooftop
Chicago Loop, Chicago · Cindy's Rooftop · 12 S Michigan Ave, Chicago, IL 60603, USA
Hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with choice seasonal fare.
void
Avondale, Chicago · void · 2937 N Milwaukee Ave, Chicago, IL 60618, USA
Trivoli Tavern
Fulton Market District, Chicago · Trivoli Tavern · 114 N Green St, Chicago, IL 60607, USA
Oysters, grills, coal-fired seafood & cocktails served amid an old-world, dark-wood interior.
Pizzeria Portofino
River North, Chicago · Pizzeria Portofino · 317 N Clark St, Chicago, IL 60654, USA
Chic Italian eatery with a riverfront terrace and patio offering craft pizza, pasta, grilled seafood, and wines.
