Deals on vacations and trips to Far Southwest Side

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Far Southwest Side flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $349, price is now $189 per person
$189
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $809, price is now $400 per person
$400
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was $1,079, price is now $604 per person
$604
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $414, price is now $241 per person
$241
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Limo/town car service, express check-in, and express check-out are also on offer.
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $736, price is now $431 per person
$431
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. There's luggage storage and multilingual staff can provide around-the-clock assistance.

Top Far Southwest Side hotels deals

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
$92 nightly
The price is $108 total per night
$108 total
Dec 7 - Dec 8
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
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
$128 nightly
The price is $145 total per night
$145 total
Dec 21 - Dec 22
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
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
$83 nightly
The price is $98 total per night
$98 total
Dec 7 - Dec 8
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
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place Chicago IL
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $121 total per night
$121 total
Nov 24 - Nov 25
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.
Free WiFi
Restaurant
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $104 total per night
$104 total
Dec 15 - Dec 16
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. WiFi in public areas is free.
Free WiFi
Air conditioning
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $115 total per night
$115 total
Nov 24 - Nov 25
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Free WiFi
Restaurant
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See all available properties in Far Southwest Side
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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 $189. 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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