Search Deals onNorth Side Vacation Packages
North Side Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,257, price is now $845 per person
$845
per person
Sep 23 - Sep 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $3,495, price is now $1,939 per person
$1,939
per person
Sep 12 - Sep 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.
Four Seasons Hotel Chicago
Downtown Chicago
Price was $4,634, price is now $2,689 per person
$2,689
per person
Sep 13 - Sep 19
found 9 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 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
Downtown Chicago
Save 100% on your flight
Price was $3,065, price is now $1,935 per person
$1,935
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,424, price is now $1,560 per person
$1,560
per person
Sep 4 - Sep 9
found 14 hours ago
Roundtrip flight included
Boston (BOS) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $2,795, price is now $1,821 per person
$1,821
per person
Sep 12 - Sep 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 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.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $2,731, price is now $1,802 per person
$1,802
per person
Sep 12 - Sep 19
found 1 day 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 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $1,952, price is now $1,319 per person
$1,319
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
3-4 Night Vacations in North Side
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in North Side
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in North Side
Yelton Manor Bed & Breakfast
140 North Shore Drive South Haven MI
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
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 ...
Victoria Resort and Bed & Breakfast
241 Oak St South Haven MI
Stay at this B&B in South Haven. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Michigan Maritime Museum and Stanley Johnson Park are ...
Save an average of 15% on thousands of hotels when you're signed in
Inn At the Park
233 Dyckman Ave South Haven MI
Stay at this B&B in South Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Michigan Maritime Museum and Stanley Johnson Park are ...
Baymont by Wyndham South Haven
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 ...
Comfort Inn & Suites
8258 Arnt Blvd Watervliet MI
Book a stay at this family-friendly hotel in Watervliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Best Western Plaza Hotel Saugatuck
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. ...
Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy
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 ...
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.
Mon, Aug 24 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$186 Roundtrip, found 1 day ago
$186
Roundtrip
found 1 day ago
Thu, Aug 27 - Sat, Aug 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$240 Roundtrip, found 1 day ago
$240
Roundtrip
found 1 day ago
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$250 Roundtrip, found 2 days ago
$250
Roundtrip
found 2 days ago
Sat, Aug 8 - Sat, Aug 15
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$399 Roundtrip, found 4 days ago
$399
Roundtrip
found 4 days ago