Southwest Side Holidays

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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 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.

Find hotels in Back of the Yards

Top hotels in Southwest Side

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is Rp2.237.494 per night from 13 Feb to 14 Feb
Rp2.237.494
Rp2.626.595 total
13 Feb - 14 Feb
includes taxes & fees
8/10 Very Good! (9,824 reviews)
Good

Reviewed on 30 Jan 2026

Congress Plaza Hotel
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St Chicago IL
Fully refundableReserve now, pay when you stay
The price is Rp1.501.405 per night from 10 Feb to 11 Feb
Rp1.501.405
Rp1.762.499 total
10 Feb - 11 Feb
includes taxes & fees
8.6/10 Excellent! (2,266 reviews)
2nd time at hotel and will come again.

Reviewed on 28 Jan 2026

DoubleTree by Hilton Chicago - Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is Rp2.326.204 per night from 5 Mar to 6 Mar
Rp2.326.204
Rp3.223.401 total
5 Mar - 6 Mar
includes taxes & fees
8.4/10 Very Good! (2,592 reviews)
The room was clean and the staff was very friendly.

Reviewed on 28 Jan 2026

Hilton Chicago
See all 5,293 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

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

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

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

What to do in Southwest Side

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

Rp413.099
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

Rp1.782.920
per adult
90% of travellers recommend
Chicago C3® by CityPASS®
Art Institute of Chicago

Art Institute of Chicago

Rp672.800
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Southwest Side

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 cancelling 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 travellers to Southwest Side during the COVID-19 outbreak?
In the face of COVID-19, travelling 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. Travellers 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 holiday 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 holiday makers 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 holiday makers 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.
What months are the cheapest to book a flight to Southwest Side?
February is the most affordable month to book a seat for your Southwest Side escape. Tickets are at their most expensive during the festive month of December, so steer clear of this time if possible.
Which airlines with flights to Southwest Side employ COVID-19 cleanliness policies?
As people begin travelling 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.

How long is a flight to Southwest Side?
Whether or not you'll have time to watch one movie or two depends on where you're flying from in the USA. To give you a rough idea, here are the average flight times for three well-known domestic routes to Southwest Side:
  • Los Angeles, CA Airport (LAX-Los Angeles Intl.) to O'Hare Intl. Airport (ORD) - 3 hours and 58 minutes
  • Denver, CO Airport (DEN-Denver Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 36 minutes
  • Minneapolis, MN Airport (MSP-Minneapolis - St. Paul Intl.) to O'Hare Intl. Airport (ORD) - 1 hour and 44 minutes

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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.