Downtown Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Downtown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$653
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) 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
$897
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) 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.
Quirky tv remote but good value would recommend solid 4 star hotel
Reviewed on Sep 10, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,470
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) 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.
Level Chicago Fulton Market
Downtown Chicago
$1,111
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The pool & jacuzzi was perfect, this hotel is beautiful
Reviewed on Sep 7, 2026
The Talbott, Autograph Collection
Downtown Chicago
$967
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) 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.
Level Chicago – Old Town
Downtown Chicago
$958
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) 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.
Location and facility was very nice
Reviewed on Sep 7, 2026
Top Hotel Deals
Old Harbor Inn
515 Williams Street South Haven MI
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 ...
Historic Hotel Nichols
201 Center St South Haven MI
Stay at this hotel in South Haven. Enjoy free WiFi, a conference center, and concierge services. Popular attractions Warner Vineyards and South Haven Center ...
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 ...
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. ...
Sun N Sand Resort
176 N. Blue Star Highway South Haven MI
Stay at this resort in South Haven. Enjoy free parking, daily housekeeping, and a picnic area. Popular attractions Kal Haven Trail and Michigan Maritime Museum ...
AmericInn by Wyndham Douglas/Saugatuck
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 ...
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 ...
Country Inn & Suites by Radisson, South Haven, MI
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 ...
Starlite Resort
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. ...
Holiday Inn Express South Haven by IHG
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 ...
Comfort Suites South Haven near I-96
1755 Phoenix Street South Haven MI
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 ...
Captain's Quarters Motel
3242 Blue Star Highway Saugatuck MI
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 ...
Great Lakes Inn and Suites
9814 M-140 South Haven MI
Stay at this motel in South Haven. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff and the overall value in our reviews. ...
Lake Bluff Inn and Suites
76648 11th Avenue South Haven MI
Book a stay at this family-friendly hotel in South Haven. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Deerlick Creek Beach Park and ...
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 ...
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.
Sat, Oct 10 - Sat, Oct 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$159
Roundtrip
found 1 hour ago
Tue, Oct 13 - Tue, Oct 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 1 hour ago
Tue, Oct 13 - Wed, Oct 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 1 hour ago
Tue, Oct 13 - Tue, Oct 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 1 hour ago
Fri, Oct 16 - Thu, Oct 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237
Roundtrip
found 1 hour ago
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