Southwest Side Holidays
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Top Flight + Hotel Deals in Southwest Side
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was €998, price is now €576 per person
€576
per person
31 Oct - 6 Nov
found 18 hours ago
Return flight included
Nashville (BNA) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Excellent staff very friendly
Reviewed on 29 Aug 2025
The Emily Hotel
Downtown Chicago
Price was €1,487, price is now €781 per person
€781
per person
31 Oct - 6 Nov
found 18 hours ago
Return flight included
Nashville (BNA) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on 22 Aug 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was €1,099, price is now €603 per person
€603
per person
31 Oct - 6 Nov
found 18 hours ago
Return flight included
Nashville (BNA) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on 27 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €2,381, price is now €1,344 per person
€1,344
per person
31 Oct - 6 Nov
found 17 hours ago
Return direct flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on 29 Aug 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was €2,650, price is now €1,559 per person
€1,559
per person
31 Oct - 6 Nov
found 17 hours ago
Return direct flight included
Nashville (BNA) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025
Where to stay in Southwest Side
Find the best Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Side
Back of the Yards
2 out of top 10 points of interest in this area
While there might not be top attractions in Back of the Yards, you can explore the larger area and discover places like Bridgeport Art Center and Zhou B Art Center.
Top hotels in Southwest Side
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €152 per night from 4 Sept to 5 Sept
€152
4 Sept - 5 Sept
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €198 per night from 15 Sept to 16 Sept
€198
15 Sept - 16 Sept
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €169 per night from 3 Sept to 4 Sept
€169
3 Sept - 4 Sept
includes taxes & fees
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.
Popular places to visit
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Southwest Side
Wendella's 90-min Chicago River Architecture Tour
€35
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
€39
per adult
96% of travellers recommend
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Flights
Holiday Rentals
General
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.