North Side Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
North Side Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was $766, price is now $592 per person
$592
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to Chicago (ORD)
Book a stay at this luxury 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,056, price is now $697 per person
$697
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) 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.
Todo estuvo genial
Reviewed on Oct 27, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,768, price is now $1,330 per person
$1,330
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Great experience and accommodations
Reviewed on Oct 27, 2026
Pendry Chicago
Downtown Chicago
Price was $1,149, price is now $869 per person
$869
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Talbott, Autograph Collection
Downtown Chicago
Price was $837, price is now $641 per person
$641
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to Chicago (ORD)
Book a stay at this luxury 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,808, price is now $1,393 per person
$1,393
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Top Hotel Deals
Yelton Manor Bed & Breakfast
140 North Shore Drive South Haven MI
0.83 km from North Side
Stay at this B&B in South Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Stanley Johnson Park and Michigan Maritime Museum are ...
Waters View Inn
86 North Shore Drive South Haven MI
1.04 km from North Side
Stay at this B&B in South Haven. Enjoy free WiFi, free parking, and a garden. Popular attractions Stanley Johnson Park and Southside Municipal Marina are located ...
Baymont by Wyndham South Haven
1555 Phoenix Rd South Haven MI
2.09 km from North Side
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 ...
Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy
117 55th St Grand Junction MI
15.82 km from North Side
Stay at this cabin in Grand Junction. Enjoy free parking, patios, and climate control. Popular attractions Saddle Lake and Upper Scott Lake are located ...
Old Harbor Inn
515 Williams Street South Haven MI
0.96 km from North Side
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 ...
Comfort Inn & Suites
8258 Arnt Blvd Watervliet MI
26 km from North Side
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. ...
Starlite Resort
3353 Blue Star Highway Saugatuck MI
28.51 km from North Side
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. ...
AmericInn by Wyndham Douglas/Saugatuck
2905 Blue Star Hwy Douglas MI
24.61 km from North Side
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 ...
Holiday Inn Express South Haven by IHG
72095 CR 388 South Haven MI
2.35 km from North Side
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 ...
Comfort Suites South Haven near I-96
1755 Phoenix Street South Haven MI
2.54 km from North Side
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 ...
Best Western Plaza Hotel Saugatuck
3457 Blue Star Highway Saugatuck MI
29.28 km from North Side
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. ...
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Jan 26 - Wed, Feb 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$150 Roundtrip, found 3 days ago
$150
Roundtrip
found 3 days ago
Tue, Dec 1 - Tue, Dec 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$235 Roundtrip, found 6 days ago
$235
Roundtrip
found 6 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$235 Roundtrip, found 3 days ago
$235
Roundtrip
found 3 days ago
Tue, Dec 1 - Tue, Dec 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$235 Roundtrip, found 6 days ago
$235
Roundtrip
found 6 days ago
Sat, Nov 21 - Tue, Dec 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$255 Roundtrip, found 5 days ago
$255
Roundtrip
found 5 days ago