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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,344, price is now $775 per person
$775
per person
Jul 4 - Jul 11
found 1 day 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 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.
Swissotel - Chicago
Downtown Chicago
Price was $1,976, price is now $1,067 per person
$1,067
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,505, price is now $852 per person
$852
per person
Jul 13 - Jul 18
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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,505, price is now $899 per person
$899
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,501, price is now $901 per person
$901
per person
Jun 4 - Jun 8
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.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $2,682, price is now $1,666 per person
$1,666
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue 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 ...
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. ...
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 ...
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 ...
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 ...
Country Inn & Suites by Radisson, South Haven, MI
1741 Phoenix St South Haven MI
2.12 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 ...
The Inn of Saugatuck
447 Butler St Saugatuck MI
28.75 km from Downtown
Stay at this B&B in Saugatuck. Enjoy free breakfast, free WiFi, and cable TV channels. Popular attractions Oval Beach and Butler Street are located nearby.
Park House Inn
888 Holland St Saugatuck MI
29.31 km from Downtown
Stay at this B&B in Saugatuck. Enjoy free breakfast, free WiFi, and free valet parking. Popular attractions Oval Beach and Butler Street are located nearby.
Comfort Inn & Suites
8258 Arnt Blvd Watervliet MI
25.03 km from Downtown
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, Jun 13 - Fri, Jul 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$166 Roundtrip, found 4 days ago
$166
Roundtrip
found 4 days ago
Sun, May 24 - Wed, Jun 10
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$169 Roundtrip, found 2 hours ago
$169
Roundtrip
found 2 hours ago
Tue, Jun 23 - Wed, Jun 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Sun, May 24 - Wed, Jun 10
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$228 Roundtrip, found 2 hours ago
$228
Roundtrip
found 2 hours ago
Sun, May 24 - Wed, Jun 10
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$228 Roundtrip, found 2 hours ago
$228
Roundtrip
found 2 hours ago