Southwest Side Vacations

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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
artist paints mural on a city street

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.

Find hotels in Back of the Yards

Find the Best Southwest Side Vacation Packages

Southwest Side Hotel Deals

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
The price is ₩127,356 per night from May 25 to May 26
₩127,356
₩196,213 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,683 reviews)
Friendly staff. Good location

Reviewed on May 5, 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is ₩198,297 per night from May 26 to May 27
₩198,297
₩235,755 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (5,167 reviews)
This hotel is conveniently located on the Riverwalk, which makes it accessible to so much. Our room was a little on the small side and the air-conditioning did not work. The staff was friendly and it’s a great location to catch an Uber.

Reviewed on May 6, 2026

River Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is ₩197,393 per night from May 27 to May 28
₩197,393
₩276,042 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,070 reviews)
Very nice and clean hotel. Wonderful break fast buffet with good selection of food.

Reviewed on May 6, 2026

Hotel Riu Plaza Chicago
See all 5,094 properties in Southwest Side
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.

Discover the most popular places to visit in Southwest Side

Navy Pier

Navy Pier

4.5/5(4,925 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park

Millennium Park

4.5/5(7,309 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park

Grant Park

4.5/5(3,360 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Frequently asked questions

Can I cancel my flight booking to Southwest Side due to COVID-19?
Our handy Customer Service Portal is where you can get important information about canceling your Southwest Side flight due to COVID-19. Before you reserve a seat, it's smart to look over the terms and conditions of your airfare too.
What's the best way to find cheap flights to Southwest Side that have flexible change policies?
We know that plans can change in the blink of an eye, so booking a flexible airfare with Expedia is always a wise idea. Tick the "No change fee" box below the "Flexible change policies" filter. Your affordable, flexible flight to Southwest Side is only a few clicks away.
What are some of the general tips for travelers to Southwest Side during the COVID-19 outbreak?
In the face of COVID-19, traveling now comes with a few extra challenges. Keep in mind these worthwhile tips before boarding your plane to Southwest Side:
  • Understand what rules and restrictions apply to both your origin and destination. It may not be possible to travel depending on local circumstances, so remember to check before you book your flight.
  • When you go through airport checkpoints, keep your face mask on. You will be asked to briefly lower it for identification purposes. Travelers who refuse to wear a face mask may face civil penalties and may also be denied boarding.
  • Instead of handing a TSA officer your boarding pass, place it directly on the reader yourself. When that's done, hold it up for inspection.
  • One container of liquid hand sanitizer is now permitted in your carry-on baggage. It must be no bigger than 12 oz (350 ml), and you'll have to take it out of your bag at the X-ray machine for screening.
  • Put any personal items (phone, wallet and keys for example) in your carry-on rather than a bin to minimize handling during the screening process.
  • If you want to take food on board, put it in a clear plastic bag and then into a screening bin. This reduces the likelihood that a TSA officer will need to touch your carry-on bag or food container for inspection.

Which airlines fly to Southwest Side?
American Airlines operates flights into or near Southwest Side, including 13307 that touch down at O'Hare Intl. Airport (ORD) each month. Work out your vacation dates and then lock in your ticket early for the biggest bargain.
How can I find cheap tickets to Southwest Side?
You'll always walk away with a fabulous deal with Expedia, but our "flexible dates" search function makes it that much easier. Enter your preferred flight date, then click on the flexible dates link above to see a list of prices for nearby days. was the best price for a flight to Southwest Side in the last seven days.
How much is a flight to Southwest Side?
There were plenty of low-cost fares up for grabs in the last seven days, with the cost of a return ticket to Southwest Side varying between and . Many lucky vacationers purchased one-way seats from () for just .
What are the most popular airports to fly into in Southwest Side?
The main entryway to Southwest Side, roughly 33491 flights service O'Hare Intl. Airport (ORD) each month. Look for a top deal, reserve your fare and get set to soak up the best of this renowned region.
When is the cheapest time to fly to Southwest Side?
If you're not set on what day you jet off to Southwest Side, try to fly out earlier in the week. The cheapest day to take off is normally Tuesday, closely followed by Monday. Saturday is typically the priciest day, with lots of vacationers choosing to fly on the weekend.
How much is a plane ticket to Southwest Side?
In the last seven days, flights to Southwest Side varied between and . Prices generally depend on the departure time, airline, cabin class and when the fare is booked.
Which airlines with flights to Southwest Side employ COVID-19 cleanliness policies?
As people begin traveling again, most commercial airlines have implemented physical distancing and other vital actions to reduce the impact of COVID-19. These carriers are among them:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.