Midwest Traveling

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Midwest Traveling

Uniquely designed vacation homes spanning over three states in the Midwest

05/15/2026

Vacation with us and L I V E like a local in the heart of Andersonville, Chicago. 🏡 Coffee on Clark Street, cozy nights in and all the charm of the North Side.

💫 Sleep 5
💫 3 bedrooms & 2 bathrooms
💫 Steps away from Clark St
💫 Few miles from Loyola & Wrigleyville

05/02/2026

Create unforgettable M E M O R I E S, not just meals 🍷🤍

Ditch the crowded restaurants and enjoy quality time with loved ones in the comfort of your vacation rental.

Our In-Home Chef Experience offers curated menus, mouth-watering flavors, and zero cleanup.

✨ Central Wisconsin Private Dining
✨ Custom & Affordable Menus
✨ Seamless Service.

Message us for more info!

04/08/2026

🌊 Beach, please!
Just a 12 minute walk to Michigan City paradise 🏖️

1.5 hours from Chicago
Sleep 10 in 4 bedrooms & 3 bathrooms

💫 Book Direct & Save 💫

04/01/2026

Escape to a themed family getaway in New Lisbon, WI, 📍 where cozy, unique and spacious homes designed for memories.

Lakefront homes perfect for exploring, relaxing and connecting with your loved ones in the heart of Wisconsin nature and only 28 miles to the Wisconsin Dells!

03/30/2026

Discover the charm of Andersonville from this stylishly designed, “impressively tranquil” retreat, perfectly positioned in the heart of Chicago’s favorite local neighborhood.

Enjoy boutique shopping, cozy cafes, and vibrant Clark Street just steps away, then return to your peaceful, sun-drenched home base.

✨Book direct and save! ✨

03/29/2026

Escape to Michigan City, IN 📍

Experience the perfect mix of sandy Lake Michigan beaches, dunes, and cozy comfort. Whether it’s a family getaway or a romantic trip, enjoy local charming shops, relaxing shorelines and stunning sunsets.

Book your friends and family vacation with us today!

Book direct and save!

11/05/2025

🎤 DrOp… fresh new garage game room comes with fresh new photos!
Shoutout to 📣 for coming through and showcasing Yeehaw Cabin!

Come and stay with us!! Save when you direct book with us!

07/19/2024

Yessss, this is real - and perfect for you - boasting a real prohibition, mobster themed 🏡 vacation rental 28 miles from the Wisconsin Dells!

Yes, you can rent it out and stay here with 15 other family members (8 adults & 8 kids sleep comfortably)
Yes, we have a 5 acre man made lake in the backyard 🏖️
Yes, we have a hot tub, kayaks, paddle board,outdoor games, plenty of space and tons of amenities!

03/16/2024

Come to Michigan City!!

Summertime is approaching and the 🏖️ and lake are waiting for you… stay with us at this beautiful home and you’ll have a short 10-12 minute walk to see it first hand.

Newly built in 2022
Sleeps 8
4 bed
2.5 bath
Hot tub, grill and screened in back patio to relax with your family and friends!

Address

Chicago, IL

Telephone

+16304053695

Website

http://midwesttraveling.com/, https://linktr.ee/midwest_traveling?utm_source=linktree_profile_share<sid=06666f0d-4b75-

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