Deals on vacations and trips to Far Southwest Side

Save when you book Far Southwest Side package deals

Choose two or more items and save on your trip:

Far Southwest Side flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Dorothy's

Dorothy's

3 out of 5
Lakeview
Save 100% on your flight
per person
Aug 16 - Aug 21
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Free WiFi in public areas, a communal living room, and luggage storage are available at this bed & breakfast. Enjoy the free continental breakfast each morning. Laundry facilities and a virtual front desk are also provided.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.
DayDreamer Domes

DayDreamer Domes

4 out of 5
Save 100% on your flight
per person
Sep 8 - Sep 14
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a garden, and a snack bar/deli are also on offer.

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
Get rates
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
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Free Cancellation
Get rates
This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.
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
Get rates
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
Get rates
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
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
Get rates
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
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-in are also provided.
Pool
Pet friendly
Don't see what you're looking for?
See all available properties in Far Southwest Side
View all properties
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

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

Carter G. Woodson Library

You can enjoy some culture when you stop by Carter G. Woodson Library in Chicago. Make some time to visit the shops while you're in the area.

Carter G. Woodson Library

Final Call Newspaper Headquarters

Find out about the history of Chicago with a stop at Final Call Newspaper Headquarters.

Final Call Newspaper Headquarters

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 $546. 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