Deals on vacations and trips to Far Southwest Side

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Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $922, price is now $626 per person
$626
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,124, price is now $726 per person
$726
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,240, price is now $804 per person
$804
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,359, price is now $890 per person
$890
per person
Aug 12 - Aug 17
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.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,130, price is now $741 per person
$741
per person
Aug 20 - Aug 24
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 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 laundry facilities.

Top Far Southwest Side hotels deals

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
The price is $184 total per night
$184 total
per night
Jun 29 - Jun 30
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
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $242 total per night
$242 total
per night
Jun 30 - Jul 1
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.
Breakfast included
Free WiFi
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Free Cancellation
The price is $183 total per night
$183 total
per night
Jun 28 - Jun 29
This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Business travelers can take advantage of the free WiFi in public areas. Self parking, express check-out, and luggage storage are also offered.
Pet friendly
Free WiFi
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $269 total per night
$269 total
per night
Jun 30 - Jul 1
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. Express check-in, express check-out, and dry cleaning are also on offer.
Pet friendly
Free WiFi
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $207 total per night
$207 total
per night
Jun 29 - Jun 30
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.
Pet friendly
Free WiFi
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
The price is $318 total per night
$318 total
per night
Jun 30 - Jul 1
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
Spa
Pet friendly
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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

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

Highland Community Bank

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

Highland Community Bank

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 $626. 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

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