North Side Vacation Packages for 2025
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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $396, price is now $291 per person
$291
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 4-star 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.
Residence Inn by Marriott Chicago Downtown / River North
Downtown Chicago
Save 100% on your flight
Price was $443, price is now $311 per person
$311
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 3.5-star 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.
Aloft Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
Price was $457, price is now $324 per person
$324
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $636, price is now $452 per person
$452
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Springhill Suites by Marriott Chicago Downtown/ River North
Downtown Chicago
Save 100% on your flight
Price was $422, price is now $301 per person
$301
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 3.5-star 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.
Pendry Chicago
Downtown Chicago
Price was $792, price is now $580 per person
$580
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Top Hotel Deals
Yelton Manor Bed & Breakfast
140 North Shore Drive, South Haven, MI
0.89 km from North Side
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 ...
Waters View Inn
86 North Shore Drive, South Haven, MI
1.04 km from North Side
Stay at this 3-star B&B in South Haven. Enjoy free WiFi, free parking, and a garden. Popular attractions Michigan Maritime Museum and Warner Vineyards are located ...
Victoria Resort and Bed & Breakfast
241 Oak St, South Haven, MI
0.16 km from North Side
Stay at this 4-star B&B in South Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Michigan Maritime Museum and Warner Vineyards ...
Baymont by Wyndham South Haven
1555 Phoenix Rd, I-196 Exit 20, South Haven, MI
2.1 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 ...
Old Harbor Inn
515 Williams Street, South Haven, MI
0.96 km from North Side
Stay at this 3-star hotel in South Haven. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean ...
Captain's Quarters Motel
3242 Blue Star Highway, Saugatuck, MI
27.55 km from North Side
Stay at this motel in Saugatuck. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
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.
Mon, Dec 22 - Wed, Dec 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 5 days ago
$172
Roundtrip
found 5 days ago
Fri, Dec 26 - Mon, Dec 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$404 Roundtrip, found 2 days ago
$404
Roundtrip
found 2 days ago
Fri, Dec 26 - Mon, Dec 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$772 Roundtrip, found 2 days ago
$772
Roundtrip
found 2 days ago
Sun, Aug 2 - Sun, Aug 16
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$883 Roundtrip, found 6 days ago
$883
Roundtrip
found 6 days ago
Sun, Aug 2 - Sun, Aug 16
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$937 Roundtrip, found 6 days ago
$937
Roundtrip
found 6 days ago