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Downtown Vacation Packages

Downtown Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
O'Hare
Save 100% on your flight
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Rosemont Theatre are located nearby.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 19 - Jul 23
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 helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
Save 100% on your flight
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star beach hotel in East Chicago. Enjoy 5 restaurants, a marina, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ameristar Casino East Chicago and Jeorse Park Beach are located nearby.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 19 - Jul 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star 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.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Jul 26 - Jul 30
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.

3-4 Night Vacations in Downtown

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Jul 26 - Jul 30
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Downtown

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)

Cheap Hotel Deals in Downtown

Old Harbor Inn

Old Harbor Inn

3 out of 5
515 Williams Street, South Haven, MI
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 ...
Old Harbor Inn
Historic Hotel Nichols

Historic Hotel Nichols

2 out of 5
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 Michigan Maritime Museum ...
Historic Hotel Nichols
Baymont by Wyndham South Haven

Baymont by Wyndham South Haven

2.5 out of 5
1555 Phoenix Rd, I-196 Exit 20, 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 ...
Baymont by Wyndham South Haven
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Postcard Cabins Barber Creek

Postcard Cabins Barber Creek

2 out of 5
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 Breedsville North Park are located ...
Postcard Cabins Barber Creek
Lake Bluff Inn and Suites

Lake Bluff Inn and Suites

2.5 out of 5
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 ...
Lake Bluff Inn and Suites
Sun N Sand Resort

Sun N Sand Resort

2.5 out of 5
176 N. Blue Star Highway, South Haven, MI
Stay at this resort in South Haven. Enjoy free parking, daily housekeeping, and a picnic area. Our guests praise the helpful staff in our reviews. Popular attractions ...
Sun N Sand Resort
Starlite Resort

Starlite Resort

2.5 out of 5
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. ...
Starlite Resort
Holiday Inn Express South Haven by IHG

Holiday Inn Express South Haven by IHG

2.5 out of 5
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 ...
Holiday Inn Express South Haven by IHG
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.

Spirit Airlines
Wed, Jul 9 - Sun, Jul 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$135 Roundtrip, found 1 day ago
$135
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Jul 9 from Los Angeles Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $135 found 1 day ago
Spirit Airlines
Tue, Jul 8 - Tue, Jul 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Los Angeles Intl. to O'Hare Intl., returning Tue, Jul 8, priced at $169 found 2 days ago
Frontier Airlines
Thu, Jun 26 - Mon, Jun 30
LAX
Los Angeles Intl.
MDW
Midway Intl.
$214 Roundtrip, found 17 hours ago
$214
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Jun 26 from Los Angeles Intl. to Midway Intl., returning Mon, Jun 30, priced at $214 found 17 hours ago
United
Sun, Jun 29 - Sun, Jul 27
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$960 Roundtrip, found 1 day ago
$960
Roundtrip
found 1 day ago
Select United flight, departing Sun, Jun 29 from Hong Kong Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $960 found 1 day ago