
Southwest Side Trips (flight + hotel)
Photo by by Midway Intl Airport
Better together
Save up to P 3,118 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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 Back of the Yards might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bridgeport Art Center and Zhou B Art Center.
Top hotels in Southwest Side

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P9,998 per night from Aug 4 to Aug 5
P9,998
P11,737 total
Aug 4 - Aug 5
includes taxes & fees
7.8/10 Good! (8,915 reviews)
"Well located for walking to Union Station, museums, restaurants, and art institute. A little difficulty getting past fences set up for Nascar event. Room temperature control (air conditioning) was on/off with no temperature control."
Reviewed on Jul 8, 2025

InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is P11,494 per night from Aug 10 to Aug 11
P11,494
P15,303 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,995 reviews)
"The property is next to most restaurants, shopping mall and walking distance to Navy Pier"
Reviewed on Jul 7, 2025

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P9,767 per night from Aug 10 to Aug 11
P9,767
P11,466 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,408 reviews)
"Front desk especially Christian was extremely helpful in getting me checked in."
Reviewed on Jul 8, 2025
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

McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Millennium Park
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Six Flags Great America
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
What to do in Southwest Side

Wendella's 90-min Chicago River Architecture Tour
P2,537
per adult
94% of travellers recommend

Chicago By Night River & Lake Cruise
P2,537
per adult
92% of travellers recommend
Frequently asked questions
More trip options
Expedia's Latest Trends
Hotels
Resorts CarmonaMadria's Pension HouseHotels in SagbayanHotels near McCormick PlaceHometown Hotel Bacolod - LacsonCrown Regency Resort & Convention CenterMarand Beach Resort Hostels BulacanSan Remigio Beach Club Sports and Leisure ResortBudget Hotels in HonoluluHotels near Teachers CampHotels with Airport Shuttle in MacauMactan-Cebu Airport Budget HotelHotel 81 DicksonLato Lato ResortMana-Mana Suites at Scarletz KLCC
Flights
Packages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.