Fall Chicago Weekend Guide

Chicago is a quick and easy flight away from Nashville, especially on Southwest. And October is the perfect month to visit (and to travel in general!) as it’s not as touristy, and the weather is comfortable. Time to pull out your favorite boots and scarves, and take a weekend getaway! I’ve got the whole weekend planned for you:

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   RL Restaurant  & Driehaus Museum

Friday – Arrive late morning

Get checked in at the Talbott Hotel, a newly renovated and charming boutique hotel. They have a darling outdoor restaurant and even offer a special autumn package so that you can experience all that Chicago has to offer during the season.

Start your weekend off right at the sophisticated RL Restaurant, a 5-minute walk from the Talbott. You won’t regret this upscale experience and tasty lunch.

After lunch, walk another short 5 minutes to the gorgeous Driehaus Museum, a home from the Gilded Age with elegant period pieces. Stepping into the museum is like stepping back in time – it fully immerses you in the late 19th century.

Walk and shop the Magnificent Mile, or take a rest back at the Talbott.

Either way, that night, walk just 5 minutes (truly, the Talbott is close to everything) and end up at Lou Malnati’s for a festive dinner and some of the best pizza you’ll ever have.

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Art Institute of Chicago  & Architecture Boat Tour


Wake up and head to the famous Art Institute of Chicago. It is gorgeous and well-worth the visit. Grab lunch at the Institute.

After lunch, head to Millennium Park to see art, architecture, landscaping, and of course, Cloud Gate (the “bean”).

Later that afternoon, do not miss an architecture boat tour. You don’t need to know anything about architecture – just go, and you’ll be enthralled. There’s simply no other way to see Chicago inside and out.

That night, after a nap at the Talbott, walk 5 minutes to Carmine’s for a fun, lively Italian dinner. Sit outside on the Italian-style patio and people watch under string lights. Dine on bread, pasta, and wine. Enjoy.

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Sunday Morning

Wake up for a little more shopping on the Magnificent Mile.

Enjoy the city sites as you walk to Eataly, a bright Italian marketplace with everything Italian you could ever dream of. Eat at the restaurant if you have time, or snag a treat for the road! The walk back to the Talbott will take you 10 minutes.

Depart midday.



Would love to hear about some of your favorite things to do in Chicago in the comments!

Love, Bee

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