Far Southwest Side Vacation Packages

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Top Far Southwest Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
The line to get coffee at the cafe downstairs was always 12 people deep. The staff was not very fast…

Reviewed on Jul. 21, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 11 - Oct 15
found 24 hours ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
A great hotel in a perfect location.

Reviewed on Jul. 22, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on Jul. 21, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
An amazing property and staff. Will be coming back!

Reviewed on Jul. 20, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,115 reviews)
Great hotel with the exception of a terribly uncomfortable bed. The mattress was incredibly firm and difficult to sleep on.

Reviewed on Jul. 21, 2025

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
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Ashburn

The restaurants and churches are just a few features travelers like about Ashburn. If you want to do some sightseeing nearby, Chicago Ridge Shopping Mall and Balzekas Museum of Lithuanian Culture are a few top places to visit.

Find hotels in Ashburn

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Far Southwest Side Hotel Deals

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 CA $184 per night from Aug 18 to Aug 19
CA $184
CA $216 total
Aug 18 - Aug 19
includes taxes & fees
7.8/10 Good! (8,930 reviews)
"Unfortunately, the hotel doesn’t offer its own parking, so I had to pay over $60 per night at a nearby garage. Also, the bathroom wasn’t very clean — we found a lot of someone else’s hair when we checked in, which was disappointing. Other than that, the stay was good. The staff at the restaurant ..."

Reviewed on Jul. 22, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is CA $341 per night from Jul 24 to Jul 25
CA $341
CA $444 total
Jul 24 - Jul 25
includes taxes & fees
9/10 Wonderful! (2,066 reviews)
"The pool was amazing!!"

Reviewed on Jul. 19, 2025

InterContinental Chicago Magnificent Mile by IHG
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 CA $196 per night from Aug 17 to Aug 18
CA $196
CA $231 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (2,494 reviews)
"Loved it!"

Reviewed on Jul. 20, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,676 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Far Southwest Side

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4.5/5(459 reviews)

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

Navy Pier
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Far Southwest Side

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Far Southwest Side

Frequently asked questions

How much does a Far Southwest Side vacation package cost?
Tailor make your Far Southwest Side vacation package from an affordable CA $767. Choose from any combination of rental cars, flights and hotels to craft the getaway you've been dreaming about. Remember to add on some activities and experiences!
How do I get a cheap travel package to Far Southwest Side?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you a nice amount too. A Far Southwest Side vacation package makes it a cinch to create your dream adventure. With more than 550 airlines all over the world to choose from, finding convenient flights that fit your schedule will be no sweat. On top of that, we have over 1,000,000 hotel options globally to pick from. Now that's what you call choice. Whatever your budget, Expedia can show you the world.
What are the top hotels in Far Southwest Side?
Check out the deals at Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton in Chester Highlands. Any good Far Southwest Side itinerary has to include a stop in this great city!
How far in advance should I book my Far Southwest Side vacation?
It can be hard to know when is the perfect time to book your Far Southwest Side trip. But typically the earlier you book, the more affordable the prices. In some cases, you can reserve your flights and hotels nearly a year prior to departure. If you're considering a last-minute getaway, no need to panic! There are incredible bargains posted on Expedia every single day.
What does an Expedia Far Southwest Side travel package include?
Flights, hotels and car rentals — we connect you to the best deals. All you'll have to do is select your favorite combination. Once you've made your booking, you can add on the fun stuff like day tours and sightseeing activities. Our travel packages make it easy to customize an awesome Far Southwest Side trip.
What should I know before booking a Far Southwest Side travel package?
Whether it's relaxation or adventure you're chasing, a Far Southwest Side vacation package lets you organize your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Far Southwest Side Expedia vacation package?
With a vacation package, you're the one in charge. Whether you want to fly to Far Southwest Side in business or coach, simply pick from the available airline options. Expedia has access to more than 550 partner airlines globally.
If I'm not able to travel, can I cancel my Far Southwest Side vacation package?
If your vacation plans in Far Southwest Side have been upended, it's good to know that it is possible to cancel your booking. If you booked less than 24 hours ago, you may be eligible to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge a fee. For more details, check our Customer Service Portal.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.