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Parkside Vacation Packages

Parkside Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott Chicago Downtown / River North

Residence Inn by Marriott Chicago Downtown / River North

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $563, price is now $406 per person
$406
per person
Apr 23 - Apr 27
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, 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.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was $798, price is now $596 per person
$596
per person
Apr 22 - Apr 26
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was $1,172, price is now $924 per person
$924
per person
Apr 22 - Apr 27
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms 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 $933, price is now $564 per person
$564
per person
Apr 15 - Apr 19
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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,696, price is now $1,145 per person
$1,145
per person
May 1 - May 5
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,419, price is now $960 per person
$960
per person
Apr 30 - May 5
found 24 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
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 $1,254, price is now $876 per person
$876
per person
May 2 - May 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,493, price is now $1,089 per person
$1,089
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) 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.

3-4 Night Vacations in Parkside

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $575, price is now $418 per person
$418
per person
May 7 - May 10
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Price was $798, price is now $596 per person
$596
per person
Apr 22 - Apr 26
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $933, price is now $564 per person
$564
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was $889, price is now $621 per person
$621
per person
May 9 - May 12
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Parkside

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 $1,244, price is now $751 per person
$751
per person
May 5 - May 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,419, price is now $960 per person
$960
per person
Apr 30 - May 5
found 24 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
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 $1,443, price is now $1,004 per person
$1,004
per person
May 5 - May 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,032, price is now $1,440 per person
$1,440
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)

Cheap Hotel Deals in Parkside

Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms ...
Opens in a new windowChicago Club Inn & Suites
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway Willowbrook IL
Stay at this hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowRed Roof Inn PLUS+ Chicago - Willowbrook
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
Book a stay at this boutique hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
Opens in a new windowThe Champagne Lodge & Luxury Suites
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Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Opens in a new windowHoliday Inn Chicago – Midway Airport S by IHG
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St Alsip IL
Book a stay at this business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowDoubleTree by Hilton Chicago - Alsip
Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave Oak Lawn IL
Book a stay at this business-friendly hotel in Oak Lawn. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
Opens in a new windowHilton Chicago/Oak Lawn
Best Western Plus Chicagoland - Countryside

Best Western Plus Chicagoland - Countryside

3.5 out of 5
6251 Joliet Rd La Grange IL
Stay at this hotel in La Grange. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Opens in a new windowBest Western Plus Chicagoland - Countryside
Motel 6 Bridgeview, IL

Motel 6 Bridgeview, IL

2 out of 5
9625 S 76th Ave Bridgeview IL
Stay at this motel in Bridgeview. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowMotel 6 Bridgeview, IL
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.

Spirit Airlines
Sat, May 9 - Sat, May 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$119 Roundtrip, found 2 days ago
$119
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, May 9 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 16, priced at $119 found 2 days ago
Frontier Airlines
Wed, Apr 15 - Mon, Apr 20
LAX
Los Angeles Intl.
MDW
Midway Intl.
$231 Roundtrip, found 4 hours ago
$231
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Apr 15 from Los Angeles Intl. to Midway Intl., returning Mon, Apr 20, priced at $231 found 4 hours ago
American Airlines
Tue, Mar 17 - Wed, Mar 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$408 Roundtrip, found 5 days ago
$408
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Mar 17 from Los Angeles Intl. to Greater Rockford, returning Wed, Mar 25, priced at $408 found 5 days ago
United
Mon, Apr 13 - Sat, May 2
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$1,020 Roundtrip, found 9 hours ago
$1,020
Roundtrip
found 9 hours ago
Select United flight, departing Mon, Apr 13 from Hong Kong Intl. to O'Hare Intl., returning Sat, May 2, priced at $1,020 found 9 hours ago