Southwest Side Holidays from £851
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top Southwest Side Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
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
Clearing
Visitors to Clearing appreciate its restaurants. A visit to Wintrust Sports Complex and SeatGeek Stadium might round out your trip if you're looking to see more of the area.
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.
Garfield Ridge
Be sure to check out the restaurants and churches while you're strolling through Garfield Ridge, and hop on the metro at Midway Station to see more of the surrounding area.
West Lawn
2 out of top 10 points of interest in this area
Travellers enjoy West Lawn for its restaurants and museums. Consider checking out Balzekas Museum of Lithuanian Culture while you're in the area.
Brighton Park
The restaurants and shopping are a few reasons travellers visit Brighton Park. Though there aren't many top sights in the neighbourhood, you can visit United Center and Bridgeport Art Center, a few notable attractions nearby.
Southwest Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Top hotels in Southwest Side
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
£155
20 Sept - 21 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£158
13 Oct - 14 Oct
includes taxes & fees
8/10 Very good! (2,245 reviews)
"Bathroom was not cleaned that well. Old carpets w stains in room. Light next to bed did not work and no one came to fix. Bar area. Cash only for 2 days since system was down. OK if no other alternatives which was our case."
Reviewed on 16 Sept 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£154
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (10,262 reviews)
"The room was very nice . Aury and bright. Staff, especially the bell hop were friendly and helpful. Only drawback was the construction on the floor above us and the price of food at the resturant. But overall a good experience."
Reviewed on 16 Sept 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.
Stay near popular Southwest Side attractions
Marquette Park
9.4/10 (3 reviews)
After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
S.S. Peter and Paul Church
After visiting S.S. Peter and Paul Church, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.
Balzekas Museum of Lithuanian Culture
10.0/10 (1 review)
You can spend time studying the exhibits at Balzekas Museum of Lithuanian Culture in Chicago. Stroll along the lakeside in this vibrant area or visit its top-notch restaurants.
Union Stock Yard Gate
You can find out about the history of Chicago with a trip to Union Stock Yard Gate.
Ephraim Bajar Cultural Center
Enjoy an outing to Ephraim Bajar Cultural Center during your stay in Chicago. Amble around the area's parks or visit its churches.
What to do in Southwest Side
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
Frequently asked questions
How much does a Southwest Side travel package cost?
The cheapest Southwest Side package is £851, so your dream escape can become a reality — without breaking the bank. Bundle flights, hotels and car rentals to build a package that's perfect for you.
If I'm not able to travel, can I cancel my Southwest Side travel package?
If your holiday plans in Southwest Side have been upended, it's comforting to know that it is possible to amend or cancel your booking. If you booked less than 24 hours ago, you may be able to get a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose a fee. For more information, check our Customer Service Portal.
How do I get a cheap travel package to Southwest Side?
Bundle your bookings with Expedia to save on your next adventure. With over 550 airlines and 1,000,000 hotels globally, your Southwest Side travel package can be customized exactly to suit your budget. With all that extra cash, why not add one or more interesting experiences and tours? It's an easy way to unlock even more discounts. That dream holiday to Southwest Side is much closer than you thought!
Does Expedia offer Book Now, Pay Later Southwest Side holidays?
Your bank balance shouldn't prevent you from escaping on holiday, so Expedia has devised a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a fantastic getaway without eating away at your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your trip. Check out these flexible payment options:
- Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's convenient monthly instalment plans. If paying a little each month works for you, pick this option at checkout.
- Pay in instalments holidays: If you'd prefer to pay for your escape in multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan with Klarna.
How far in advance should I book my Southwest Side holiday?
To bag discount prices, book early. Air carriers usually release flights, along with some of the lowest fares, nearly 12 months ahead of time. Hotels, car rental and experiences should also be booked early to avoid disappointment. If you're in need of a last-minute getaway to Southwest Side, there are always plenty of great deals on Expedia. Check them out now!
What does an Expedia Southwest Side travel package include?
Much of that is up to you. You can choose from a variety of Southwest Side packages, such as a hotel, flight and rental car. You can also book a flight with a hotel, or a rental car and a flight. Once you've made your booking, you can add on the fun stuff like tours and activities. Whatever your Southwest Side break looks like, you're sure to save!
What should I know before booking a Southwest Side travel package?
Bundling your bookings into a Southwest Side travel package is the most convenient way to organise your trip. Not only that, you'll save big just for combining your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Southwest Side Expedia travel package?
Most definitely. We have access to over 550 partner airlines throughout the world, so you can customize your Southwest Side trip according to your style and budget.
Explore a world of travel with Expedia
- 5 Star Hotels in Chicago
- Gay-Friendly Hotels in Armour Square
- Serviced Apartments in Chicago
- Sports Hotels in Chicago
- Beach Resorts & in Chicago
- Boutique Hotels in Chicago
- Cheap Hotels in Chicago
- Family-Friendly Hotels in Chicago
- Hotels Suites in Chicago
- Hotels with Pool in Chicago
- Luxury Hotels in Chicago
- Spa Hotels in Chicago
- Chicago Hotels
- Hotels near Chicago Union Station
- Cicero Hotels
- Downtown Chicago Hotels
- Hotels near Grant Park
- Red Roof Inn Hotels in Hyde Park
- Hyde Park Hotels
- Destination Hotels in Kenwood
- Gay-Friendly Hotels in Kenwood
- Little Village Hotels
- Lower West Side Hotels
- Magnificent Mile Hotels
- Hotels near McCormick Place
- Hotels near Midway Intl.
- North Lawndale Hotels
- Hotels near Northwestern Memorial Hospital
- Hotels near Soldier Field
- The Loop Hotels
- Hotels near University of Chicago
- West Loop Hotels
- Flights to Chicago
- Flights to Cicero
- Flights to South Side
- American Airlines Dublin (DUB) to Chicago (ORD) flights
- British Airways London (LHR) to Chicago (ORD) flights
- Delta Atlanta (ATL) to Chicago (MDW) flights
- Delta Lagos (LOS) to Chicago (MDW) flights
- Porter Airlines Toronto (YTZ) to Chicago (MDW) flights
- United Houston (IAH) to Chicago (MDW) flights
- Virgin Atlantic London (LHR) to Chicago (MDW) flights
- Flights from Chicago
- Flights from Dublin (DUB) to Chicago (ORD)
- Flights from Edinburgh (EDI) to Chicago (ORD)
- Flights from Galesburg (GBG) to Chicago (MDW)
- Flights from Glasgow (GLA) to Chicago (MDW)
- Flights from Glasgow (GLA) to Chicago (ORD)
- Flights from New York (JFK) to Chicago (MDW)
- Flights from London (LGW) to Chicago (MDW)
- Flights from London (LGW) to Chicago (ORD)
- Flights from London (LHR) to Chicago (MDW)
- Flights from London (LHR) to Chicago (ORD)
- Flights from Manchester (MAN) to Chicago (MDW)
- Flights from Manchester (MAN) to Chicago (ORD)
- Flights from St. Cloud (STC) to Chicago (MDW)
- Flights from Tulsa (TUL) to Chicago (ORD)
- Art Institute of Chicago
- Blue Island Holidays
- Visit Downtown Chicago
- Visit Grand Boulevard
- Chicago Harbor Lighthouse
- Visit Little Village
- Chicago Riverwalk
- Visit South Loop
- Visit The Loop
- Chicago Theatre
- Chicago Water Tower
- Chicago Holidays
- Visit Chicago
- Cibc Theatre
- Cicero Holidays
- Downtown Chicago Holidays
- Ernest Hemingway Museum and House
- Garfield Park Conservatory
- Grant Park
- Hillside Holidays
- Lakeview Holidays
- Lincoln Hall
- Lincoln Park Conservatory
- Lincoln Park Zoo
- Lincoln Park Holidays
- Romantic Holiday Packages Far Southwest Side
- Michigan Avenue
- Millennium Park
- Montrose Beach
- Navy Pier
- Visit Oak Park
- Robie House
- Shops at North Bridge
- The Loop Holidays
- Unity Temple
- Willis Tower
- Wrigley Field
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
