Search Deals on
South Side Vacation Packages

South Side Flight + Hotel 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 $479, price is now $334 per person
$334
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,599, price is now $927 per person
$927
per person
Nov 12 - Nov 17
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,651, price is now $1,060 per person
$1,060
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $694, price is now $459 per person
$459
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $932, price is now $623 per person
$623
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $574, price is now $392 per person
$392
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $492, price is now $344 per person
$344
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $683, price is now $479 per person
$479
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

3-4 Night Vacations in South Side

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $441, price is now $294 per person
$294
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $519, price is now $335 per person
$335
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $833, price is now $552 per person
$552
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Villa Christina

Villa Christina

3 out of 5
Greater Grand Crossing
Save 100% on your flight
Price was $677, price is now $460 per person
$460
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in South Side

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $694, price is now $459 per person
$459
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,059, price is now $1,190 per person
$1,190
per person
Nov 12 - Nov 17
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,599, price is now $927 per person
$927
per person
Nov 12 - Nov 17
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,651, price is now $1,060 per person
$1,060
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Cheap Hotel Deals in South Side

Baymont by Wyndham South Haven

Baymont by Wyndham South Haven

2.5 out of 5
1555 Phoenix Rd South Haven MI
Book a stay at this business-friendly hotel in South Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Opens in a new windowBaymont by Wyndham South Haven
Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
117 55th St Grand Junction MI
Stay at this cabin in Grand Junction. Enjoy free parking, patios, and climate control. Popular attractions Saddle Lake and Upper Scott Lake are located ...
Opens in a new windowPostcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy
Starlite Resort

Starlite Resort

2.5 out of 5
3353 Blue Star Highway Saugatuck MI
Stay at this motel in Saugatuck. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowStarlite Resort
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
8258 Arnt Blvd Watervliet MI
Stay at this hotel in Watervliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowComfort Inn & Suites
Old Harbor Inn

Old Harbor Inn

3 out of 5
515 Williams Street South Haven MI
Stay at this hotel in South Haven. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowOld Harbor Inn
Comfort Suites South Haven near I-96

Comfort Suites South Haven near I-96

2.5 out of 5
1755 Phoenix Street South Haven MI
Book a stay at this business-friendly hotel in South Haven. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff in ...
Opens in a new windowComfort Suites South Haven near I-96
AmericInn by Wyndham Douglas/Saugatuck

AmericInn by Wyndham Douglas/Saugatuck

3 out of 5
2905 Blue Star Hwy Douglas MI
Book a stay at this business-friendly hotel in Douglas. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Opens in a new windowAmericInn by Wyndham Douglas/Saugatuck
Holiday Inn Express South Haven by IHG

Holiday Inn Express South Haven by IHG

2.5 out of 5
72095 CR 388 South Haven MI
Book a stay at this business-friendly hotel in South Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Opens in a new windowHoliday Inn Express South Haven by IHG
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.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Fri, Nov 13 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, just found
$197
Roundtrip
just found
Select American Airlines flight, departing Fri, Nov 13 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 13, priced at $197 just found
United
Fri, Nov 13 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, just found
$197
Roundtrip
just found
Select United flight, departing Fri, Nov 13 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 13, priced at $197 just found
Southwest Airlines
Thu, Nov 26 - Tue, Dec 1
LAX
Los Angeles Intl.
MDW
Midway Intl.
$227 Roundtrip, found 8 hours ago
$227
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Thu, Nov 26 from Los Angeles Intl. to Midway Intl., returning Tue, Dec 1, priced at $227 found 8 hours ago
Philippine Airlines
Fri, Nov 13 - Wed, Dec 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$928 Roundtrip, found 10 hours ago
$928
Roundtrip
found 10 hours ago
Select Philippine Airlines flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Wed, Dec 2, priced at $928 found 10 hours ago