We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
The latest reviews. The lowest prices. The perfect place to shop for hotels.

“Best Sandwich of the Year!”

Windy City Red Hots
Ranked #15 of 213 Restaurants in Leesburg
Cuisines: American, Fast Food
More restaurant details
Restaurant details
Good for: Families with children
Dining options: Dinner, Lunch, Outdoor Seating, Reservations, Seating, Takeout
Level Contributor
150 reviews
108 restaurant reviews
common_n_restaurant_reviews_1bd8 44 helpful votes
“Best Sandwich of the Year!”
Reviewed October 15, 2012

We were in historic Leesburg to poke around the shops and ran into a couple on the street who just had lunch at Windy City Red Hots. Although they live in Baltimore, they come here periodically for their Chicago-style sandwich fix. We took their recommendation (specifically for the italian beef sandwich, dipped) and popped inside. It's a a small cheery space with Chicago memorobilia, about 12 seats, with another dozen outside behind the restaurant. My italian sandwich bundle of love arrived wrapped in wax paper, and words do not do it justice. Shaved seasoned beef in a wonderful roll, perfectly sopped in au jus, but not to the point of falling apart. Best sandwich of the year, hands down. The staff were great and they had a nice selection of microbew beer to compliment the food. Leesburg will without a doubt be a regular destination. Soooo good!

  • Visited October 2012
    • Value
    • Atmosphere
    • Service
    • Food
2 Thank misterduffy
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Write a Review

75 reviews from our community

Visitor rating
Rating summary
Date | Rating
  • English first
  • Any
English first
Round Hill, Virginia
Level Contributor
43 reviews
35 restaurant reviews
common_n_restaurant_reviews_1bd8 34 helpful votes
“Like being in Chicago”
Reviewed August 26, 2012

Windy City makes FANTASTIC, authentic Italian beef sandwiches. Additionally, they serve polish sausage, italian sausage, and hot dogs made the right way (the Chicago way). If you go, make sure to get your beef wet with sweet peppers and provolone cheese: you won't be dissapointed.

Visited August 2012
1 Thank ddjetsetters
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Silver Spring MD
Level Contributor
38 reviews
27 restaurant reviews
common_n_restaurant_reviews_1bd8 24 helpful votes
“Just like Chicago...what no White Sox!”
Reviewed July 23, 2012

I had read about this place in the Washington Post and really wanted to visit but it's about 50 miles from our home in Maryland. We went to the outlet mall in Leesburg last Saturday and planned to have lunch at Windy City Red Hots to see if it measured up to the places my wife and I remembered in Chicago. I had a hot dog with everything on it and it was very good (came back for a second one). My wife had an Italian Sausage which she also said was very good (but a little small). We each had a Bells Amber Ale (love Bell's beers!). There are only 3 tables and a several stools at a counter facing the window. They also sell Vienna sport peppers and Vienna Chicago style relish (both of which are a must for a Chicago dog) and I bought a jar of each. The place has photos of Chicago plus Bear, Bulls, Cubs, and Blackhawk images....I told the owner I would send him a White Sox pennant (since they have actually won a World Championship recently) for his wall to make Windy City Red Hots complete!

  • Visited July 2012
    • Value
    • Atmosphere
    • Service
    • Food
Thank Georgespicer
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Level Contributor
182 reviews
103 restaurant reviews
common_n_restaurant_reviews_1bd8 79 helpful votes
“Chicago in a Leesburg Style Bun”
Reviewed April 3, 2012

Not the best Chicago style dog I've ever had but when you are in Northern Virginia and have a cravings its not too bad. Colleagues had the Italian Beef and liked it too.
Not a lot of seating (maybe 12 total seats) so dont expect comfort if you get their at peak hours.

  • Visited April 2012
    • Value
    • Atmosphere
    • Service
    • Food
Thank OrmondBeachFL
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

Travelers who viewed Windy City Red Hots also viewed

Leesburg, Loudoun County
Leesburg, Loudoun County
Leesburg, Loudoun County

Been to Windy City Red Hots? Share your experiences!

Write a Review Add Photos & Videos

Owners: What's your side of the story?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing