Search Deals onDowntown Vacation Packages
Downtown 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 $645, price is now $446 per person
$446
per person
Oct 29 - Nov 2
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
Save 100% on your flight
Price was $1,113, price is now $654 per person
$654
per person
Oct 29 - Nov 2
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.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,551, price is now $960 per person
$960
per person
Oct 14 - Oct 18
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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,863, price is now $1,183 per person
$1,183
per person
Oct 27 - Nov 3
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. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,554, price is now $1,001 per person
$1,001
per person
Oct 28 - Nov 3
found 17 hours 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,388, price is now $936 per person
$936
per person
Oct 14 - Oct 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 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.
Holiday Inn Chicago North-Evanston by IHG
Downtown Evanston
Save 100% on your flight
Price was $1,191, price is now $832 per person
$832
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ryan Field and Baha'i House of Worship are located nearby.
LIVN - Millennium Park Downtown Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,646, price is now $1,850 per person
$1,850
per person
Oct 10 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
3-4 Night Vacations in Downtown
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Downtown
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Downtown
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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. ...
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 ...
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.
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$138 Roundtrip, just found
$138
Roundtrip
just found
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Mon, Sep 28 - Tue, Oct 6
LAX
Los Angeles Intl.
MDW
Midway Intl.
$261 Roundtrip, found 1 hour ago
$261
Roundtrip
found 1 hour ago
Fri, Nov 13 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,066 Roundtrip, found 2 days ago
$1,066
Roundtrip
found 2 days ago
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