Chicago's Streeterville from the Water Tower to Navy Pier

Michigan Avenue and the Water Tower

The Chicago Water Tower and Chicago Avenue Pumping Station (Michigan and Chicago Avenues) is the oldest thing in Streeterville by a century. The tower is Gothic, castellated, built of yellow Joliet limestone, with a crenellated turret and traffic passing it on both sides. Its matching pumping station stands across the street and now holds Lookingglass Theatre, back in business after a hiatus. You can look at the outside for nothing, at any hour, and the City Gallery on the tower's ground floor is also free and open daily. It is one small room, about as long a visit as a coffee.

The Magnificent Mile (North Michigan Avenue) is Streeterville's western edge and the reason many visitors come at all, thirteen blocks of limestone and glass canyon. Walking it costs nothing. Water Tower Place, with its seven-storey atrium and glass elevators, is 30% vacant and entering a $170m rebuild. Put your browsing hour into 900 North Michigan, where Bloomingdale's sits under a rotunda, and The Shops at North Bridge.

360 CHICAGO (North Michigan Avenue) has a glass-walled deck on the 94th floor of the black steel X-braced former John Hancock tower. You look straight down the lakefront from it, and it is the better of the city's two big decks. Tickets start at $30 for adults online. The TILT platform, a $45 add-on, tips you face-down over Michigan Avenue at 1,030 feet. Every ticket now needs a timed-entry reservation, so book your slot before you leave the hotel. The old Signature Room restaurant upstairs closed for good in 2023; the deck and CloudBar are what remain.

The Museum of Contemporary Art

Museum of Contemporary Art Chicago stands back from the street behind a monumental granite staircase, a boxy Kleihues building of aluminium panels and glass. A four-storey atrium carries daylight through the middle of it, and the sculpture terrace at the rear faces Lake Shore Park. It is one of the largest contemporary art spaces in the United States and it carries the neighbourhood's cultural weight. Admission is $22 for adults, and Illinois residents go free on Tuesdays. It closes Mondays and stays open late on Tuesdays. Parties of 10 or more should book in advance for the reduced rate, and can add a docent tour when they do.

Navy Pier end to end

Navy Pier (Streeter Drive) is free to walk on, and nobody checks anything at the gate. You enter past the Polk Bros Park fountain, pass under the arcs of the Pepsi Wave Wall, and finish at the barrel-vaulted domed Aon Grand Ballroom at the far end. The white 196ft Centennial Wheel turns above the middle of it, with enclosed gondolas, from $19. Come on a clear evening in summer, when fireworks go up over the water twice a week. Coaches drop off on Streeter Drive.

Chicago Children's Museum (Navy Pier Family Pavilion) has a three-storey climbing schooner with rope rigging running up through its atrium. Children dig in the Dinosaur Expedition fossil pit and work the channels and pumps of Water Works. Entry is $25, or $21 for Illinois residents, and every child has to be with an adult of 18 or older. It closes Tuesdays, and on Monday, Wednesday and Thursday it shuts at 2 p.m. Check the day before you walk over, because this is the wet-weather plan families fall back on.

Chicago Shakespeare Theater (north side of Navy Pier) occupies a glass-fronted block looking out over the lake. The 500-seat Jentes Courtyard wraps timber galleries around a thrust stage, and The Yard rearranges movable seating towers for whatever is on. Shakespeare on a pier over Lake Michigan is an odd and brilliant pairing. Seats run $45 to $100. The 75-minute adaptations are the ones to take if you landed that morning, and the group sales desk handles parties of 10 or more across the three house sizes.

Offshore Rooftop (far east end of Navy Pier) is a seventh-floor terrace with water on three sides and the skyline framed to the west. Teal banquettes and firepits sit behind collapsible floor-to-ceiling glass walls, which is how it keeps trading through a Chicago winter; Guinness recognises it as the world's largest rooftop bar. Off-season hours are Thursday to Sunday only. After 9 p.m. the door is 21 and over. In summer a Tock reservation is all but mandatory. $$$.

The architecture river tour from the pier

Shoreline Sightseeing (Navy Pier dock) ties its low open-top white-and-blue cruisers up a short walk from the Centennial Wheel. The 75-minute architecture tour is $50 for adults, and passengers spend much of it craning upward as the boat slides under the raised steel bascule deck of the Michigan Avenue bridge. Take it before you do anything else in the city; the buildings make more sense afterwards. Sailings run March to November and are trimmed to 60 minutes in the cold months. The Navy Pier dock is the wheelchair-accessible one, and the operator runs group rates and private charters.

Olive Park and Ohio Street Beach

Milton Lee Olive Park and Ohio Street Beach is where people go when the pier gets too full. Five circular granite fountains sit ringed by honey locust trees on a spit of land behind the Jardine Water Plant, and a crescent of sand curves north from it. The skyline stands head-on across open water with nothing in front of it, and this is the best free photograph in Streeterville. The park is free, open daily, takes no bookings and closes at 8 p.m. Lifeguards are on the beach from late May to Labor Day.

Tables on Michigan, Grand and Ohio

The Purple Pig (off Michigan Avenue) works out of a sunken paved plaza under a pig-silhouette sign at Streeterville's southwest corner. Order a dozen small plates off the chalked board of smears and fried things, and ask for the house-cured charcuterie, which arrives whole on butcher paper. The format suits a mixed table better than any steakhouse on the strip. It is walk-in heavy and the queue is famous, so arrive at opening or eat late. In warm weather the plaza patio takes the overflow. $$.

Gino's East - Magnificent Mile has marker graffiti over its booths and walls, top to bottom, across three floors. The deep dish lands in a blackened steel pan with a cornmeal crust, and it bakes 45 to 60 minutes, so order it the moment you sit down. Mozzarella sticks have their own following here. A comedy bar runs downstairs and there is a terrace on the third floor. This is the deep-dish rite of passage without the trek out of the neighbourhood. $$.

Volare Ristorante Italiano (off Grand Avenue) is a corner room behind a brick-walled courtyard patio under an awning. Tables are tight and white-clothed under a low ceiling, and waiters carve at the table. It has been running since 1997 and locals still book it. Dinner only, from 4 p.m., and from 3 p.m. Friday to Sunday. The room is small and busy; book well ahead for anything more than four. $$$.

Sayat Nova (Ohio Street) sits half a step below the pavement in a dim street-level room, with carved dark-wood partitions between the booths, brass and patterned rugs. Charcoal-grilled kebab platters come with rice, alongside mezza spreads. The family has had it open since 1965 and the Magnificent Mile two blocks west has not touched it. The booths seat about six, and a bigger table is worth a phone call first. Closed Monday and Tuesday. $$.

Lizzie McNeill's on the river bank

Lizzie McNeill's Irish Pub (north bank of the Chicago River) is a low-slung pub at the foot of the Streeterville high-rises, with two string-lit patios, the Lake Shore Drive bridge overhead and boats passing at eye level. It is the best outdoor pint in the neighbourhood and the natural end of a walk along the water. The patios only run May to October. Doors stay open until 1:30 a.m., and 2:30 a.m. on Saturday. The Chicago Riverwalk proper begins a few minutes west along the same bank. $$.

Where to stay

InterContinental Chicago Magnificent Mile is the 1929 Medinah Athletic Club tower, carrying Assyrian-style terracotta reliefs and a golden onion dome. Guests swim on the 14th floor in the junior-Olympic pool where Johnny Weissmuller trained, lined with blue Spanish majolica tile, with a terracotta Neptune fountain on the end wall. A full renovation landed in 2023. Rooms run $250 to $450 a night depending on season. Holy Name Cathedral is a five-minute walk west, and the Chicago Architecture Center is one bridge south across the river.

Opening days and booking

The Museum of Contemporary Art closes Mondays, the Children's Museum closes Tuesdays and shuts early three days a week, and Sayat Nova closes Monday and Tuesday. Reserve 360 CHICAGO's timed entry and an Offshore table through Tock before you travel, and call Volare well in advance for a larger table.

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