1. Dorothy's

- Location: Lakeview
- Guest rating: 8.6/10 (Excellent, 197 reviews)
- Price: CA $38, CA $94 total, includes taxes & fees, Dec 14 - Dec 15, for Our top choices for Indian Head Park bed & breakfast
- Review: I enjoyed my stay, by Kellen
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Check prices for these dates, December 13–14, 2026









Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.






If you want to find a place to stay with a small number of rooms and a more personalized environment, a B&B might be just the right fit for your vacation to Indian Head Park. If you're interested in discovering some top attractions, Soldier Field and United Center are worth a stop.
Every B&B has its own unique feel. Whether it's a picturesque garden or a beautiful dining room, the little details are what make bed and breakfasts a home away from home.
Below are some B&Bs in the surrounding area: The Sono Chicago: 7 rooms. 16.1 mi (25.9 km) from the heart of Indian Head Park. Enjoy the rooftop terrace and fireplace in the lobby. The Villa Toscana: 9 rooms. 17.4 mi (28 km) from the downtown core. Dorothy's: 7 rooms. Situated 17.4 mi (28 km) from the heart of Indian Head Park. Ray's Bucktown B&B: 11 rooms. 15 mi (24.2 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. Harvey House Bed & Breakfast: 5 rooms. Located 9.7 mi (15.5 km) from the core of Indian Head Park. Enjoy the deli and unique décor.
When you're dreaming of a trip to Indian Head Park, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. Average annual precipitation for Indian Head Park is 49 inches.
You can map out your trip in and around Indian Head Park ahead of time with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 7.9 mi (12.8 km) from the city center. Otherwise, you can search for flights to Chicago O'Hare Intl. Airport (ORD), which is 14.3 mi (22.9 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.