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Downtown Vacation Packages

Downtown Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
Price was $650, price is now $478 per person
$478
per person
Jun 28 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Prospect Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Rob Roy Golf Course and Northbrook Sports Complex are located nearby.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,754, price is now $1,032 per person
$1,032
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,311, price is now $1,562 per person
$1,562
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Lodge Geneva National

Lodge Geneva National

4 out of 5
Save 100% on your flight
Price was $1,857, price is now $1,307 per person
$1,307
per person
Jul 2 - Jul 9
found 20 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Book a stay at this golf resort in Lake Geneva. Enjoy an outdoor pool, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant in our reviews. Popular attractions Geneva Lake and Geneva National Golf Club are located nearby.
The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,513, price is now $1,072 per person
$1,072
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $815, price is now $587 per person
$587
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Save 100% on your flight
Price was $1,772, price is now $1,303 per person
$1,303
per person
Jul 2 - Jul 9
found 20 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Stay at this hotel in Lake Geneva. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Geneva National Golf Club and Lake Como are located nearby.
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,104, price is now $819 per person
$819
per person
Jun 17 - Jun 21
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, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

3-4 Night Vacations in Downtown

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
Price was $745, price is now $559 per person
$559
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $963, price is now $624 per person
$624
per person
Jun 22 - Jun 25
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Lakeview
Save 100% on your flight
Price was $1,408, price is now $1,042 per person
$1,042
per person
Jun 25 - Jun 28
found 15 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,021, price is now $776 per person
$776
per person
Jun 18 - Jun 21
found 9 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.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,754, price is now $1,032 per person
$1,032
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,088, price is now $1,250 per person
$1,250
per person
Jun 17 - Jun 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,936, price is now $1,198 per person
$1,198
per person
Jul 4 - Jul 11
found 16 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,351, price is now $1,459 per person
$1,459
per person
Jun 17 - Jun 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 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 ...
Opens in a new windowOld 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 South Haven Center ...
Opens in a new windowHistoric Hotel Nichols
Baymont by Wyndham South Haven

Baymont by Wyndham South Haven

2.5 out of 5
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 ...
Opens in a new windowBaymont by Wyndham South Haven
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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. ...
Opens in a new windowStarlite Resort
Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy

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 ...
Opens in a new windowPostcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy
Best Western Plaza Hotel Saugatuck

Best Western Plaza Hotel Saugatuck

2.5 out of 5
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. ...
Opens in a new windowBest Western Plaza Hotel Saugatuck
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 ...
Opens in a new windowHoliday Inn Express South Haven by IHG
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 ...
Opens in a new windowLake Bluff Inn and Suites
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.

Frontier Airlines
Wed, May 27 - Fri, May 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 9 hours ago
$132
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, May 27 from Los Angeles Intl. to O'Hare Intl., returning Fri, May 29, priced at $132 found 9 hours ago
Delta
Wed, Jul 22 - Wed, Jul 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$219 Roundtrip, found 2 days ago
$219
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jul 22 from Los Angeles Intl. to Midway Intl., returning Wed, Jul 29, priced at $219 found 2 days ago
United
Wed, Nov 4 - Mon, Nov 9
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$359 Roundtrip, found 3 days ago
$359
Roundtrip
found 3 days ago
Select United flight, departing Wed, Nov 4 from Los Angeles Intl. to South Bend Intl., returning Mon, Nov 9, priced at $359 found 3 days ago
American Airlines
Sun, May 24 - Sun, May 31
LAX
Los Angeles Intl.
RFD
Greater Rockford
$404 Roundtrip, found 1 day ago
$404
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, May 24 from Los Angeles Intl. to Greater Rockford, returning Sun, May 31, priced at $404 found 1 day ago