From Windy City to River City – Your Guide to a Richmond, VA Getaway

Busy work schedules, extracurricular activities, family obligations – life is busy! If you’re anything like us, you start planning a getaway as soon as a coveted free weekend is spotted on the calendar.

Recently dubbed “a hidden culinary gem” by Forbes magazine, Richmond, VA, is quickly becoming a hot spot for travelers while maintaining its small town, Southern hospitality. Not only will gourmands love the Southeastern capital – history buffs, outdoor enthusiasts, and art collectors (or browsers) will no doubt be charmed by Richmond and its locals.

With a quick two-hour direct flight from Chicago O’Hare to Richmond, you’ll enjoy the James River’s beautiful view before lunch. Read on to discover why Richmond is the perfect weekend getaway for Chicagoans.

Food & Beverage Scene

Few culinary destinations have garnered as much attention as Richmond has in the last five years. Even before the pandemic wreaked havoc on the restaurant industry, Richmond had solidified itself as a foodie destination. Never one to back down, Richmond came out of Covid stronger than ever thanks to inspired local chefs, sommeliers, and restaurateurs, all of whom have taken the local dining scene to new heights.

With over 900 restaurants, you could spend more than two years eating dinner out without visiting the same establishment twice! And in addition to the sheer impressiveness of the number of restaurants in a relatively small city, Richmond is home to seven James Beard Award-nominated restaurants, including Lehja, Sub Rosa Bakery, Mekong, Mama J’s Kitchen, L’Opposum, Peter Chang and Brenner Pass.

richmond vineyard

With over 40 craft breweries, eight cideries, and dozens of wineries and wine bars in Richmond, you’ll never go thirsty.

How to try it all:

Discover Richmond offers food tours of unique neighborhoods in Richmond. Choose from the Church Hill, Carytown, Art District, or Scott’s Addition food tour. Offering walking and biking tours, you’ll meet the chefs and restauranteurs behind Richmond’s diverse culinary scene and try their signature dishes.


Richmond is a natural playground for adventure lovers. Whether you love to bike, raft, hike, run or climb – there is something for everyone!

richmond river

Don’t be surprised if you see a kayaker whitewater rafting or a guided rafting tour making its way downtown – the James River runs through Richmond with class III and IV rapids. Alongside the James, you’ll find the Capital Trail, a dedicated, paved pedestrian and bike trail connecting downtown Richmond to Williamsburg. You’ll find historic sites, eateries, and picnic spots along the way.

Don’t miss it:

The James River Park System is a 600-acre urban oasis. A preserved island in the center of the James downtown, Belle Isle is the park’s most popular site, offering wooded paths, mountain biking trails, historical areas, fishing, and a granite wall for rock climbing.


Few places in America are as richly decorated with historical landmarks as Richmond, where you can literally stand where history happened. Historical markers line city streets and country roads, with 13 Civil War battlefield sites, hundreds of historically significant buildings and homes, and several museums to explore.

Walk the cobblestoned streets of Church Hill to St. Johns Church, where Patrick Henry delivered his famous “Give Me Liberty Or Give Me Death” speech. Explore Henricus Historical Park to see where Pocahontas lived, or walk the Richmond Slave Trail and trace the steps of thousands of enslaved workers.

How to see it all:

See the sights and learn about Richmond’s 400 years of history on a narrated classic vintage trolley with RVA On Wheels. Visiting during the warmer months? Venture Richmond offers historically narrated boat tours of the James River and Kanawha Canal along downtown Richmond’s historical canal walk.

Art Scene

Like so many historical cities, Richmond’s art and cultural scene was born from the heartaches of war and thrived in the creative and diverse landscape that shapes Richmond. Murals cover the walls of local restaurants and shops, and major art museums, many of which are free, draw national attention to the city.

After visiting the Virginia Museum of Fine Arts, head next door and enjoy the Virginia Museum of History and Culture. Finish your museum tour at the Institute for Contemporary Art at Virginia Commonwealth University.

Once you’ve made your way through the museums, visit over 70 art galleries sprinkled throughout downtown. But don’t assume the art is only indoors – Richmond is a living canvas, with over 100 murals decorating the streets, created by local and international artists.

Don’t miss it:

The Arts District of Richmond hosts the First Friday art walk year-round. The galleries, shops, and restaurants on and around Broad St. open their doors to celebrate art and the community.

Where to Stay

The Quirk Hotel in downtown Richmond is a chic boutique-like hotel celebrating the local art scene throughout the hotel and within its art gallery in the lobby. Recently named one of Condé Nast Travelers’ “Best New Hotels in the World,” you can’t go wrong with this whimsical space.

Looking for something more historic? Check out the Linden Row Inn or The Jefferson Hotel.

Contact your Windy City Travel advisor to plan your perfect getaway to Richmond!