Deals on vacations and trips to Far Southwest Side

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Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $622, price is now $396 per person
$396
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $969, price is now $556 per person
$556
per person
Mar 25 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $744, price is now $441 per person
$441
per person
Mar 25 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $665, price is now $397 per person
$397
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $844, price is now $539 per person
$539
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

Top Far Southwest Side hotels deals

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$164 nightly
The price is $192 total per night
$192 total
Jan 19 - Jan 20
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
Pool
Hot Tub
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $105 total per night
$105 total
Jan 25 - Jan 26
Total with taxes and fees
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Pet friendly
Free WiFi
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $103 total per night
$103 total
Jan 30 - Jan 31
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-in, and express check-out are also on offer.
Pet friendly
Free WiFi
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$168 nightly
The price is $192 total per night
$192 total
Jan 18 - Jan 19
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.
Pool
Spa
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
900 E Grand Chicago IL
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $153 total per night
$153 total
Jan 20 - Jan 21
Total with taxes and fees
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Free WiFi
Restaurant
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $110 total per night
$110 total
Jan 19 - Jan 20
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
Pool
Breakfast included
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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

Highland Community Bank

Learn about the local history of Chicago when you take a trip to Highland Community Bank.

Highland Community Bank

Dr. Percy Julian Residence

Find out about the history of Chicago when you take a trip to Dr. Percy Julian Residence. Make some time to visit the shops while you're in the area.

Dr. Percy Julian Residence

Advocate High Tech Medical Center

Though Advocate High Tech Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Chicago while you are here.

Advocate High Tech Medical Center

Frequently asked questions

How much are vacation packages to Far Southwest Side?
With a Travelocity vacation package, you could paint the town red in Far Southwest Side for a mere $396. Flights, hotels and tours — we're a one-stop shop for all of them. You can save some cash just for bundling together your bookings. And with everything taken care of before you even set off, you won't have a care in the world.
Where can I get the best vacation package deals for Far Southwest Side?
Travelocity has endless ways to score an incredible Far Southwest Side package deal. Choose from as many as 400 airlines and 1,000,000 properties around the world and create a travel itinerary that's right for you. With this amount of choice, now's the time to book your next big adventure.
Why should I purchase my Far Southwest Side vacation bundle via Travelocity?
Travel is all about making fantastic new memories and leaving all your stresses behind — which is why we provide you with a professional team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our terrific range of getaway packages. So what are you waiting for? There's no time like the present to secure that vacation you've always dreamed of.
Can I save on my Far Southwest Side car rental if I book it with hotels and flights?
You sure can with our Far Southwest Side vacation packages. With one of these, there are lots of ways to make your vacation budget go further. Combine any two or more car, flight, hotel and tour bookings and see the savings grow. With your own ride, all the main sights in and around Far Southwest Side are a memorable road trip away.
Which airport is best for Far Southwest Side?
You'll find there are three main options for those heading to and from Far Southwest Side — O'Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT).
What is there to do in Far Southwest Side?
Far Southwest Side has hidden gems at every turn, however ensure you plan a trip to Highland Community Bank and Carter G. Woodson Library while you're in town. These two attractions are popular with visitors.

Photos of local treasures

Browse Far Southwest Side vacation photos for more inspiration

Photo by Steve Luzzo
Photo by Steve Luzzo

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