A Local's Guide to Chicago

The Windy City can easily sweep you off your feet. Chicago has 26 miles of shoreline on Lake Michigan, man-made marvels like Willis Tower and Frank Lloyd Wright’s Robie house, plus fantastic food, art and comedy scenes. Architecture buffs love the city, and if you rent a place for a few days, you’ll get to experience it up close. HGTV designer Tiffany Brooks has lived in and around Chicago her whole life, and she and her fellow HGTV star Alison Victoria, a Chicago native, have plenty of suggestions for visitors. Read on for their favorite spots.

Your Tour Guides: Tiffany Brooks, Designer, HGTV Smart Home 2023 + Alison Victoria, Host, Windy City Rehab

Get to Know Chicago

• Population: 2.7 million

• Nickname: The Windy City is actually not the windiest city in the United States. It doesn’t even make the top 10!

• Cultural claim to fame: The Art Institute of Chicago holds the largest collection of works by Monet outside of Paris.

• Famous firsts: Ferris wheel and skyscraper

What to See

Chicago Architecture Center River Cruise: Take in the city’s beautiful buildings by boat and get all the history behind them. “I’ve done this tour multiple times because the guides are a wealth of knowledge,” says Alison.

Navy Pier: “You can’t miss the giant Ferris wheel,” says Tiffany. The Centennial Wheel stands nearly 200 feet high and has climate-controlled gondolas so you can ride any time of year.

Skydeck Observation Deck at Willis Tower: Beam up to the 103rd floor of Chicago’s tallest building to experience a view like no other. “It’s an amazing way to see the city,” says Tiffany. On a clear day, you may spot nearby states Indiana, Wisconsin and Michigan.

Where to Shop

Jayson Home: The ritzy Lincoln Park neighborhood is a must-visit, and so is this furniture and decor store, set inside a 20,000-square-foot former warehouse. “It’s my go-to for gifts and everything home,” says Alison.

Randolph Street Market: This flea market is so much more than a place to shop, says Tiffany. In addition to vintage clothes and home goods, you’ll find food trucks and live music as part of the market’s 20th anniversary celebration.

Scout: Go here for a highly curated antiques shopping experience, says Tiffany. “It’s not one of those places where you have to sift through stuff — every single item feels like a score.”

Where to Eat

Little Goat Diner: Breakfast is served all day at this elevated diner. “It’s American cuisine done soulfully. You have to try the French toast and fried chicken,” says Tiffany.

Le Bouchon: Teleport to Paris at this quaint Bucktown spot, which has been a Chicago mainstay since 1993. “It’s the best French food in Chicago,” says Alison.

Chicago Pizza and Oven Grinder Co.: “This place is famous for its pizza pot pies, which I prefer over deep dish,” says Tiffany. Lines are long, so get there early, and keep in mind it’s cash only.

Where to Stay

Lincoln Park Condo: Many sites are walkable from this apartment. The zoo is just five minutes away. Sleeps 4, $250 per night (average rate), #2449258 on vrbo.com

West Loop Loft: Big groups can spread out in this modern, newly renovated space. It’s 2,500 square feet! Sleeps 12, $570 per night (average rate), #7954627ha on vrbo.com

Three-Story Charmer: Exposed brick and colorful decor make this spot near the United Center extra homey. Sleeps 10, $500 per night (average rate), #2679936 on vrbo.com

Logan Square Apartment: The railroad-style floor plan here includes a cute balcony off the back. Sleeps 4, $166 per night (average rate), #9420291ha on vrbo.com

Streeterville Corner Unit: The building’s rooftop offers 360-degree views of the city and Lake Michigan. Sleeps 6, $483 per night (average rate), #9590634ha on vrbo.com

Bucktown Beauty: Enjoy the bustling neighborhood, then sleep peacefully thanks to insulated windows. Sleeps 4, $194 per night (average rate), #3244651 on vrbo.com