Deals on vacations and trips to Southwest Side

Save when you book Southwest Side package deals

Choose two or more items and save on your trip:

Southwest Side flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Downtown Chicago
Save 100% on your flight
Price was $774, price is now $464 per person
$464
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Chicago (ORD)
This hotel features a restaurant, a coffee shop, and free WiFi in public areas. Express check-out, luggage storage, and free newspapers are also on offer.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,298, price is now $845 per person
$845
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,252, price is now $836 per person
$836
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Chicago (ORD)
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.
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 $1,233, price is now $839 per person
$839
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,102, price is now $759 per person
$759
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.

Top 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
$135 nightly
The price is $161 total per night
$161 total
Sep 7 - Sep 8
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
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $181 total per night
$181 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A lobby fireplace, luggage storage, and wedding services are also on offer.
Pet friendly
Free WiFi
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $193 total per night
$193 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and limo/town car service are also offered.
Free airport shuttle
Pet friendly
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$206 nightly
The price is $245 total per night
$245 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. Self parking, a lobby fireplace, and luggage storage are also offered.
Pet friendly
Free WiFi
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$251 nightly
The price is $298 total per night
$298 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's in-room fitness on site, and concierge services and wedding services are also offered.
Pet friendly
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
Reserve now, pay when you stay
$152 nightly
The price is $181 total per night
$181 total
Aug 23 - Aug 24
Total with taxes and fees
This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the 8 conference rooms, free WiFi in public areas, and express check-out. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and wedding services.
Pet friendly
Free WiFi
Don't see what you're looking for?
See all available properties in 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.

Stay near popular Southwest Side attractions

Marquette Park

9.4/10 (3 reviews)
After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
See properties

Frequently asked questions

How much are vacation packages to Southwest Side?
Epic adventures await in Southwest Side, with Travelocity vacation packages starting at just $464. Providing both hotels and flights, these sensational deals make it a cinch to see all corners of the globe.
Where can I get the best vacation package deals for Southwest Side?
It's simple — look no further than Travelocity. With no less than 400 partner airlines and 1,000,000 worldwide properties, it's easy to put together a Southwest Side package deal that suits your travel style.
Why should I purchase my Southwest Side vacation package with Travelocity?
Whether you're searching for the ultimate unplugged vacation or you crave the hustle and bustle of the big city, booking everything with Travelocity saves you time, hassle and money. No need to sift through hundreds of websites looking for the best deal — our Price Match Guarantee ensures you'll never be out of pocket, and our team of customer service experts are available 24/7 should you need anything at all.
Can I save on my Southwest Side car rental if I book it with my hotel or flight?
Sure can. And our Southwest Side vacation packages are the perfect way to do it. With only a few clicks you can save money as well as time by booking everything in one place. Collect the keys to your rental car and feel the freedom of the open road. Searching for things to do? Add some tours or experiences to your package and make savings on those too.
Which airport is best for Southwest Side?
For anyone heading to and from Southwest Side, the most used airports are O'Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT).
What is there to do in Southwest Side?
Southwest Side boasts hidden surprises at every corner, but be sure you plan a visit to both S.S. Peter and Paul Church and Balzekas Museum of Lithuanian Culture while you're here. These attractions are very popular with visitors to the region.

Photos of local treasures

Browse Southwest Side vacation photos for more inspiration

An airplane exhibit labeled "Concourse A" in an airport terminal.
An indoor space with a large airplane model suspended from the ceiling, a sign reading "Concourse A", and a display of various aircraft.
A modern building with a clock tower and a glass facade.
An aircraft's underside with propellers and landing gear, inside a hangar with a high ceiling and windows.
An indoor exhibit with a large informational display about the Battle of Midway Memorial.

Explore More Ways to Travel with Travelocity