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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
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12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Browse Select Southwest Side Villas

HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12
Outdoor dining

HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12

10.0 out of 10, Exceptional, (8)
"Great property and very kind and responsive hosts. I would be happy to stay here again. "
HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12
Charming Retreat in the Heart of Des Plaines by RedAwning
TV, video games, offices

Charming Retreat in the Heart of Des Plaines by RedAwning

8.0 out of 10, Very good, (12)
"Location was great and house was clean."
Charming Retreat in the Heart of Des Plaines by RedAwning
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.
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Top Southwest Side Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Nice and very clean. Friendly and helpful staff. Very close to bus stop (bus 20) takes you to Magnificent Mile, The Bean…and bus 8 took us right to Rate field for a White Sox game. Just blocks down from Randolph Ave… lots of fun outdoor eateries!! Only recommendation- don’t take a room next to elevator because you’ll hear it go up and down ALL night long."
Betty 3-night trip
Posted 11 hours ago
Crowne Plaza Chicago West Loop by IHG