Far Southwest Side Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 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 Far Southwest Side

Find the best Far Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Far Southwest Side
Default Image

Ashburn

The restaurants and churches are a few reasons travellers visit Ashburn. Though there aren't many top sights in the neighbourhood, you can visit Chicago Ridge Shopping Mall and Childrens Museum of Oak Lawn, a few notable attractions nearby.

Find hotels in Ashburn

Top hotels in Far 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 ฿4,301 per night from 11 May to 12 May
฿4,301
฿5,113 total
11 May - 12 May
includes taxes & fees
8/10 Very Good! (10,197 reviews)
Old and historic property. With that being said, not all of the property is renewed but the rooms are kept clean :) service is good and is close to a lot of things in downtown chicago

Reviewed on 10 May 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ฿4,813 per night from 25 May to 26 May
฿4,813
฿5,722 total
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (4,285 reviews)
Lovely place to stay. Very clean and staff was so polite and helpful!!

Reviewed on 9 May 2026

Hilton Chicago/Magnificent Mile Suites
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ฿4,797 per night from 25 May to 26 May
฿4,797
฿6,621 total
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,100 reviews)
Good breakfast, limited hours. Rooms are clean and new

Reviewed on 10 May 2026

Hotel Riu Plaza Chicago
See all 4,774 properties in Far 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

Wrigley Field

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

Wrigley Field
Navy Pier

Navy Pier

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

Navy Pier
Millennium Park

Millennium Park

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

Millennium Park

What to do in Far Southwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

฿862
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

฿1,405
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS®: Experience 5 must-see attractions

฿4,598
per adult
94% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
See all activities in Far Southwest Side

Frequently asked questions

Can I cancel my flight booking to Far Southwest Side due to COVID-19?
If you've yet to book your tickets, check the terms and conditions of the airfare you're considering. If you've already reserved your flight to Far Southwest Side, make use of our Customer Service Portal. It will help determine which COVID-19 policies are applicable to your reservation and provide you with the next steps.
What's the best way to find cheap flights to Far Southwest Side that have flexible change policies?
When it comes to travelling these days, flexibility is crucial. That's why we've added a "No change fee" filter to help you locate cheap and flexible tickets to Far Southwest Side. It's near the top left of your screen directly under the "Flexible change policies" heading.
What are some of the general tips for travellers to Far Southwest Side during the COVID-19 outbreak?
COVID-19 has ushered in dramatic changes to how we travel. If you're planning an escape to Far Southwest Side, these tips will help you navigate these new rules and challenges:
  • Before you lock in a flight, check if any travel restrictions apply — in both your origin and destination. Stay informed with the latest updates by reviewing government travel advisories.
  • When you go through airport screening, keep your face mask on. You will be required to lower it briefly to verify your identity. Passengers who refuse to wear a mask may be fined and denied boarding.
  • Rather than handing a TSA agent your boarding pass, position it directly on the reader yourself. After that, hold it up for inspection.
  • TSA is now permitting passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on bags. This will have to be removed from your bag for scanning.
  • Place any personal items (e.g, keys, phone and wallet) in your carry-on rather than a bin to reduce handling during the screening process.
  • Separate any food you have for X-ray screening. Putting it in a clear plastic bag and into a bin reduces the need for a TSA employee to handle and inspect your belongings.

Which airlines fly to Far Southwest Side?
Organise your seat with American Airlines and then start putting together your Far Southwest Side travel itinerary. This leading carrier provides 13307 flights every month to O'Hare Intl. Airport (ORD), a main gateway.
How can I find cheap tickets to Far Southwest Side?
In the last seven days, was the lowest price for a flight to Far Southwest Side. For an even cheaper fare, book well ahead of time and be flexible with your dates. Search for your trip to Far Southwest Side, then compare prices for nearby days by clicking on the "flexible dates" link above.
How much is a flight to Far Southwest Side?
In the last seven days, round-trip airfares to Far Southwest Side sold from just and reached a maximum price of . For one-way fares taking off from (), the cheapest seat during this time was only .
What are the most popular airports to fly into in Far Southwest Side?
Start arranging your Far Southwest Side holiday by booking a fare on one of the 33491 flights each month to O'Hare Intl. Airport (ORD). This is the region's main entry point.
When is the cheapest time to fly to Far Southwest Side?
If you'd prefer to spend your holiday money enjoying the best of Far Southwest Side rather than on your flight there, jet off earlier in the week. The most affordable day to travel is normally Tuesday, with Monday a close second. With many folks travelling over the weekend, Saturday often has the highest ticket prices.
How much is a plane ticket to Far Southwest Side?
Fares to Far Southwest Side varied from to in the last seven days. Typically, the quicker you book the better the price.
Which airlines with flights to Far Southwest Side employ COVID-19 cleanliness policies?
As countries begin to open their borders, most airlines have resumed business with new measures including physical distancing and enhanced disinfection measures. Here's what different carriers are doing to ease the spread of COVID-19:
  • 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.

Explore a world of travel with Expedia

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