Far Southwest Side Holidays

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Top Flight + Hotel Deals in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Sept - 10 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
Hotel was great for the price. Close to Michigan and there’s plenty of food options that are walking distance. Rooms are ok, they could use a fridge and microwave for those who like to reheat their food or store any groceries they may buy if staying for a few days. (This is a preference). Overall, I enjoyed my stay.

Reviewed on 19 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Sept - 10 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
The property was very clean and well-maintained, offering an amazing view that made our stay truly memorable. Highly recommend for anyone looking for a relaxing and scenic getaway

Reviewed on 18 Jul 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Sept - 10 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
We were happy with every aspect of our stay!

Reviewed on 19 Jul 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Sept - 10 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
Staff was super helpful.

Reviewed on 17 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Sept - 10 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Amazing place overall

Reviewed on 15 Jul 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 a few reasons travellers visit Ashburn. Though there aren't many top sights in the neighbourhood, you can visit Chicago Ridge Shopping Mall and Balzekas Museum of Lithuanian Culture, 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 €179 per night from 4 Aug to 5 Aug
€179
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,985 reviews)
"Historic hotel!"

Reviewed on 16 Jul 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
Fully refundable
The price is €299 per night from 19 Aug to 20 Aug
€299
19 Aug - 20 Aug
includes taxes & fees
9/10 Wonderful! (2,063 reviews)
"Convenient"

Reviewed on 17 Jul 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 €148 per night from 10 Aug to 11 Aug
€148
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (2,474 reviews)
"Rocky was awesome and gave us great recommendations. Check in lady was nice and had no issues. Only issue we had was the bar. My husband waiting a good 30 min with no acknowledgment and it wasn’t busy. This happened 2 nights in a row. Someone from the food area noticed he hadn’t been helped and helped ..."

Reviewed on 18 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,671 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 featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(40 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(125 reviews)

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

Navy Pier
Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home 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

€41
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€38
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

€38
per adult
92% 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 holiday package cost?
Tailor make your Far Southwest Side holiday package from an affordable €643. 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 holiday 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 holiday?
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 favourite 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 holiday package lets you organise 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 holiday package?
With a holiday 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 holiday package?
If your holiday 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.