8 days in Chicago & Virginia Beach Itinerary

8 days in Chicago & Virginia Beach Itinerary

Created using Inspirock United States attractions planner

This plan was created by another user.  Make it your plan

Route & dates

8 days in Chicago & Virginia Beach Itinerary

Start: Chicago
1
Chicago
— 3 nights
Fly:  4​h 30​min
2
Virginia Beach
— 3 nights
Fly:  4​h 30​min
End: Chicago

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, historic sites, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, take in the waterfront at Navy Pier, explore and take pictures at Wrigley Field, and engage your brain at Museum of Science and Industry.

For photos, ratings, traveler tips, and tourist information, you can read our Chicago road trip app .

The Route module can give you travel options from your home to Chicago. Expect a daytime high around 83°F in August, and nighttime lows around 67°F. Wrap up your sightseeing on the 13th (Tue) to allow time to travel to Virginia Beach.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trip

Frank Lloyd Wright's Unity Temple
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Wrigley Field ©
Wrigley Field

3
nights
Virginia Beach

Virginia Beach ©
Holding a record for the longest pleasure beach in the world, Virginia Beach showcases 35 miles of coastline and maintains a longstanding reputation as a family-friendly vacation destination.
You'll find plenty of places to visit near Virginia Beach: Bacon's Castle (in Surry), Williamsburg (Colonial Williamsburg, Jamestown Settlement, & more) and St. Luke's Historic Church & Museum (in Smithfield). There's still lots to do: take in the waterfront at Virginia Beach Boardwalk, tour the pleasant surroundings at The Noland Trail, admire the masterpieces at Chrysler Museum of Art, and learn about all things military at Military Aviation Museum.

To find ratings, where to stay, other places to visit, and other tourist information, use the Virginia Beach tour itinerary planning app .

Traveling by flight from Chicago to Virginia Beach takes 4.5 hours. Alternatively, you can drive; or take a train. You'll lose 1 hour traveling from Chicago to Virginia Beach due to the time zone difference. August in Virginia Beach sees daily highs of 86°F and lows of 72°F at night. Cap off your sightseeing on the 17th (Sat) early enough to travel back home.

Things to do in Virginia Beach

Museums Historic Sites Theme Parks

Side Trips

Williamsburg, The Noland Trail, Chrysler Museum of Art, St. Luke's Historic Church & Museum, Bacon's Castle
Highlights from your plan
St. Luke's Historic Church & Museum ©
Colonial Williamsburg ©
Colonial Williamsburg
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg

Similar Plans

11 days in Chicago BY A USER FROM UNITED STATES June, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: June, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 12 days in Virginia Beach & Richmond BY A USER FROM UNITED STATES June, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: June, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 10 days in Chicago BY A USER FROM CANADA June, kids, culture, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: June, kids, culture, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 9 days in Chicago BY A USER FROM UNITED STATES July, teens, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: July, teens, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Chicago BY A USER FROM UNITED ARAB EMIRATES July, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: July, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 11 days in Chicago & Racine BY A USER FROM ARGENTINA June, culture, outdoors, relaxing, romantic, beaches, museums, shopping, popular & hidden gems PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 30 days in United States BY A USER FROM UNITED KINGDOM July, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife, popular sights PREFERENCES: July, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 9 days in Chicago BY A USER FROM CYPRUS November, culture, outdoors, relaxing, romantic, beaches, shopping, wildlife, popular sights PREFERENCES: November, culture, outdoors, relaxing, romantic, beaches, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Chicago BY A USER FROM UNITED STATES August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular sights PREFERENCES: August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 6 days in Virginia Beach BY A USER FROM UNITED STATES June, teens, kids, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: June, teens, kids, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 14 days in Chicago BY A USER FROM UNITED STATES July, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: July, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 11 days in United States BY A USER FROM UNITED STATES July, kids, culture, outdoors, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: July, kids, culture, outdoors, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium
View more plans