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.
Illinois Beach Hotel
Save 100% on your flight
Price was $453, price is now $300 per person
$300
per person
May 19 - May 23
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Zion. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Illinois Beach State Park and Carmel Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,167, price is now $636 per person
$636
per person
May 19 - May 23
found 15 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $2,487, price is now $1,456 per person
$1,456
per person
Jun 4 - Jun 9
found 21 hours ago
Roundtrip flight included
Raleigh (RDU) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,967, price is now $1,238 per person
$1,238
per person
Jun 4 - Jun 9
found 21 hours ago
Roundtrip flight included
Raleigh (RDU) 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $728, price is now $470 per person
$470
per person
May 19 - May 23
found 15 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,003, price is now $652 per person
$652
per person
May 19 - May 23
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Top Hotel Deals
Old Harbor Inn
515 Williams Street South Haven MI
0.45 km from Downtown
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
0.39 km from Downtown
Stay at this hotel in South Haven. Enjoy free WiFi, a conference center, and concierge services. Popular attractions Warner Vineyards and South Haven Center ...
Starlite Resort
3353 Blue Star Highway Saugatuck MI
29.41 km from Downtown
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. ...
Baymont by Wyndham South Haven
1555 Phoenix Rd South Haven MI
1.74 km from Downtown
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
15.8 km from Downtown
Stay at this cabin in Grand Junction. Enjoy free parking, patios, and climate control. Popular attractions Saddle Lake and Breedsville North Park are located ...
Holiday Inn Express South Haven by IHG
72095 CR 388 South Haven MI
1.94 km from Downtown
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 ...
Captain's Quarters Motel
3242 Blue Star Highway Saugatuck MI
28.46 km from Downtown
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 ...
Lake Bluff Inn and Suites
76648 11th Avenue South Haven MI
3.28 km from Downtown
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 ...
DayDreamer Domes
397 Blue Star Hwy South Haven MI
5.16 km from Downtown
Stay at this hotel in South Haven. Enjoy free breakfast, free parking, and room service. Popular attractions Kal Haven Trail and Michigan Maritime Museum are ...
AmericInn by Wyndham Douglas/Saugatuck
2905 Blue Star Hwy Douglas MI
25.53 km from Downtown
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 ...
Best Western Plaza Hotel Saugatuck
3457 Blue Star Highway Saugatuck MI
30.19 km from Downtown
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.
Wed, May 6 - Wed, May 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$128 Roundtrip, found 3 hours ago
$128
Roundtrip
found 3 hours ago
Wed, Apr 29 - Tue, May 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Sat, May 9 - Sat, May 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 3 hours ago
$183
Roundtrip
found 3 hours ago
Sat, May 9 - Sat, May 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 3 hours ago
$237
Roundtrip
found 3 hours ago
Wed, May 13 - Sat, May 16
LAX
Los Angeles Intl.
MDW
Midway Intl.
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago