Chicago, Illinois, Destination Guide

Chicago, Illinois, Destination Guide

Bordering Lake Michigan in Illinois, Chicago is the Midwest’s largest city. Steeped in magnificent architecture, renowned art museums, world-class eateries, and so much more, Chi-Town knows a thing or two about being one of the USA’s liveliest cities in America. Read below for HAP’s official guide to the “Windy City.”

Where to Stay:

Credit: Nigel Barker

21c Museum Hotel Chicago

Located just steps from Chicago’s Magnificent Mile shopping district in River North, 21c Museum Hotel is a unique contemporary art museum and boutique stay highlighting Chicago’s prolific artist community with its 10,000 square feet of gallery space and year-round rotating exhibitions. The 297 guestrooms boast spacious quarters packed with swarthy comfortable accommodations: plush living room seating and bedroom furnishings, white marbled bathrooms, brass light fixtures, and floor-to-ceiling windows give way to city views of Downtown Chicago.

Pendry Chicago

Pendry Chicago is one of the most luxurious hotels in Chicago’s Loop neighborhood. Its original 1929 Art Deco Carbide & Carbon Building façade leads to its swanky lobby and moody Bar Pendry. Modern design decorates each space within the newly renovated guestrooms and suites: bright white walls, swarthy-toned living room seating, and expansive windows allow for sweeping views of the “Windy City” skyline.

Where to Eat: 

Lure Fishbar

Lure Fishbar at 21c Museum Hotel Chicago

Lure Fishbar is the NYC-born restaurant that serves world-class seafood and sushi within a debonair space, made possible by dimly lit light fixtures, dark-hued seating areas, and nautical-adjacent decor that pairs perfectly with its acclaimed seafood-inspired fare. A must-have menu shareable item to start the night is the Lobster Mac, comprising white cheddar, parmesan, and fresh main lobster.


Marisol, the premiere restaurant and bar set in the Museum of Contemporary Art Chicago, is a farm-to-table establishment run by Chicagoan Executive Chef Jason Hammel. Expect seasonal dishes and punchy-colored interiors designed by artist Chris Ofili.

The Wiener’s Circle 

Comical surly staffers serve impeccable hot dogs in a tiny space that’s open late. It’s a Chicago institution — ensure you’re good with profanity before visiting. 

Pizano’s Pizza & Pasta

Pizano’s is a family-owned restaurant steeped in Italian-Chicago tradition that serves Chicago’s famed deep dish-style pizza

Where to Drink:

The Violet Hour Chicago

Nestled in the heart of Wicker Park Chicago, The Violet Hour is a James Beard Award-winning bar featuring a season-rotating cocktail list and a robust spirits selection. Dramatic violet-tinted velvet curtains hide three interior salons that glow under candlelight, providing the perfect backdrop for sipping libations.

Bar Pendry Chicago

Tucked aside from the Pendry Chicago’s lobby sits Bar Pendry: the eponymous hotel’s classic, intimate cocktail bar. The double-sided fireplace is flanked by a dimly lit bar and sumptuous lounge seating. On a chilly “Windy City” day, the Hennything is Possible, made with mulled wine, Hennessy VSOP Cognac, and fall spices, served hot sounds just right.

What to Do:

Walk Michigan Avenue’s Magnificent Mile

Spanning across a 13-block stretch of North Michigan Avenue, The Magnificent Mile features several of Chicago’s famed city sites: the Chicago River, Chicago Water Tower, the neo-Gothic Tribune Tower, the Wrigley Building skyscraper, and the 100-story John Hancock Center to name a few. From luxury shops — including Burberry, Shinola, and Marcus — to posh hotels — think the Chicago Athletic Association, Pendry Chicago, and Thompson Chicago — this truly mile-long walking path is magnificent in more ways than one.

Visit Storied Jazz Clubs such as The Green Mill

Chi-Town’s jazz music roots run deep in jazz-focused lounges like The Green Mill. History buffs will relish in the establishment’s rumored booth that’s said to have been reserved by Al Capone during the 20th-century Prohibition era. Jazz and cheap drinks flow throughout the evening here.

Visit the Cloud Gate at Millenium Park

Chicago’s most iconic park is beautiful to visit in all seasons, whether it’s winter ice skating, movies in the park, or free summer festivals. Snapping a picture by the gleaming Cloud Gate sculpture (aka “the Bean”) before picnicking on the expansive lawn beside Pritzker Pavilion is an ideal way to experience this outdoor space.

Spend an Afternoon at Garfield Park Conservatory

Garfield Park Conservatory is Chicago’s most extensive urban botanical garden. Visitors can explore the diverse flora and fauna comfortably from its indoor glass atrium-covered space or across 10 acres of outdoor gardens.

Visit the John Hancock Center

Overlook the Chicago cityscape from this 100-story skyscraper in the Magnificent Mile district. Head to the 94th floor to experience the 360 Chicago Observatory and elevated cocktail lounge, CloudBar.

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