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North Side Vacation Packages

North Side Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Four Points by Sheraton Chicago O'Hare Airport

Four Points by Sheraton Chicago O'Hare Airport

3 out of 5
O'Hare
per person
Jun 18 - Jun 22
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 15 - Jun 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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
per person
Jun 24 - Jun 30
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3.5-star 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.
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG

3.5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 29
found 6 hours ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Tinley Park. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Odyssey Fun World and Credit Union 1 Amphitheatre are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Save 100% on your flight
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Schaumburg. Enjoy free parking, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and LEGOLAND® Discovery Center are located nearby.
Embassy Suites by Hilton Chicago Naperville

Embassy Suites by Hilton Chicago Naperville

3.5 out of 5
Save 100% on your flight
per person
Jun 18 - Jun 22
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Nike Sports Complex are located nearby.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

3-4 Night Vacations in North Side

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Chicago-Carol Stream

Hampton Inn Chicago-Carol Stream

2.5 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Embassy Suites by Hilton Chicago Naperville

Embassy Suites by Hilton Chicago Naperville

3.5 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hotel Indigo Naperville Riverwalk by IHG

Hotel Indigo Naperville Riverwalk by IHG

3.5 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
per person
Jul 4 - Jul 7
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

5-7 Night Vacations in North 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
per person
Jun 15 - Jun 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
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
per person
Jun 24 - Jun 30
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

Cheap Hotel Deals in North Side

Victoria Resort and Bed & Breakfast

Victoria Resort and Bed & Breakfast

4 out of 5
241 Oak St, South Haven, MI
Stay at this 4-star B&B in South Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Michigan Maritime Museum and Kal Haven Trail are ...
Victoria Resort and Bed & Breakfast
Yelton Manor Bed & Breakfast

Yelton Manor Bed & Breakfast

3 out of 5
140 North Shore Drive, South Haven, MI
Stay at this 3-star B&B in South Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Michigan Maritime Museum and Warner Vineyards ...
Yelton Manor Bed & Breakfast
Baymont by Wyndham South Haven

Baymont by Wyndham South Haven

2.5 out of 5
1555 Phoenix Rd, I-196 Exit 20, 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 ...
Baymont by Wyndham South Haven
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Country Inn & Suites by Radisson, South Haven, MI

Country Inn & Suites by Radisson, South Haven, MI

2.5 out of 5
1741 Phoenix St, 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 ...
Country Inn & Suites by Radisson, South Haven, MI
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. ...
Starlite Resort
Best Western Plaza Hotel Saugatuck

Best Western Plaza Hotel Saugatuck

2.5 out of 5
3457 Blue Star Highway, Saugatuck, MI
Stay at this hotel in Saugatuck. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Best Western Plaza Hotel 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 ...
Holiday Inn Express South Haven by IHG
AmericInn by Wyndham Douglas/Saugatuck

AmericInn by Wyndham Douglas/Saugatuck

2 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 ...
AmericInn by Wyndham Douglas/Saugatuck
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.

Frontier Airlines
Wed, May 28 - Sat, May 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$91 Roundtrip, found 2 days ago
$91
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, May 28 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 31, priced at $91 found 2 days ago
Frontier Airlines
Wed, May 28 - Tue, Jun 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$214 Roundtrip, found 23 hours ago
$214
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Wed, May 28 from Los Angeles Intl. to Midway Intl., returning Tue, Jun 3, priced at $214 found 23 hours ago
Bargain Flight
Thu, Jun 26 - Sun, Jun 29
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$367 Roundtrip, found 1 day ago
$367
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Thu, Jun 26 from Los Angeles Intl. to South Bend Intl., returning Sun, Jun 29, priced at $367 found 1 day ago
American Airlines
Wed, Jun 18 - Wed, Jul 9
LAX
Los Angeles Intl.
AZO
Kalamazoo-Battle Creek Intl.
$375 Roundtrip, found 6 days ago
$375
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Jun 18 from Los Angeles Intl. to Kalamazoo-Battle Creek Intl., returning Wed, Jul 9, priced at $375 found 6 days ago