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Oak Street Beach Vacation Packages

Oak Street Beach Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Mundelein/Libertyville Area

Super 8 by Wyndham Mundelein/Libertyville Area

2 out of 5
per person
Dec 23 - Dec 31
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this business-friendly motel in Mundelein. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Lakeview Beach and Dock and Cuneo Mansion and Gardens are located nearby.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Home2 Suites by Hilton Lincolnshire Chicago

Home2 Suites by Hilton Lincolnshire Chicago

3 out of 5
Save 100% on your flight
per person
Dec 23 - Dec 31
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Lincolnshire. Enjoy free parking, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Marriott Theatre and Par-King Skill Golf are located nearby.
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
per person
Dec 27 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clark Street Beach and Halim Time & Glass Museum are located nearby.
Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 5 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Indigo Chicago-Vernon Hills, an IHG Hotel

Hotel Indigo Chicago-Vernon Hills, an IHG Hotel

3.5 out of 5
Save 100% on your flight
per person
Dec 23 - Dec 31
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 3.5-star boutique hotel in Vernon Hills. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Cuneo Mansion and Gardens and Conway Farms Golf Club are located nearby.
Sophy Hyde Park

Sophy Hyde Park

4 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Soldier Field and Grant Park are located nearby.
Baymont by Wyndham Gurnee

Baymont by Wyndham Gurnee

2.5 out of 5
Save 100% on your flight
per person
Dec 23 - Dec 31
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Six Flags Great America and Gurnee Mills are located nearby.
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 5 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

4 out of 5
per person
Dec 27 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and LEGOLAND® Discovery Center are located nearby.
DoubleTree by Hilton Chicago - North Shore Conference Center

DoubleTree by Hilton Chicago - North Shore Conference Center

4 out of 5
per person
Dec 27 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Skokie. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions North Shore Center for the Performing Arts and Adagio Teas are located nearby.

3-4 Night Vacations in Oak Street Beach

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

Hilton Chicago

4 out of 5
Downtown Chicago
per person
Dec 26 - Dec 29
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
per person
Dec 26 - Dec 29
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
Downtown Chicago
per person
Dec 26 - Dec 29
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Dec 26 - Dec 29
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Oak Street Beach

Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
per person
Dec 27 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Dec 27 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Oak Street Beach Last Minute Hotel Deals

The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
The Westin Michigan Avenue Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
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 ...
Congress Plaza Hotel
Thompson Chicago, by Hyatt
Thompson Chicago, by Hyatt
4.5 out of 5
21 East Bellevue, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a fitness center, and valet parking (surcharge). Our guests praise the bar and the helpful staff ...
Thompson Chicago, by Hyatt
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Eurostars Magnificent Mile
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection
3.5 out of 5
105 E Delaware Pl, Chicago, IL
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the restaurant and the helpful ...
The Whitehall Hotel, BW Premier Collection
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
Hotel Felix River North/Magnificent Mile
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Hilton Chicago/Magnificent Mile Suites
See all 3,683 properties in Oak Street Beach
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.

Book the perfect getaway to Oak Street Beach

With Hotwire, booking your next trip to Downtown Chicago is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Oak Street Beach while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Oak Street Beach flight and hotel package for as low as $293.

Living it up in Downtown Chicago means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Oak Street Beach, Downtown Chicago vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Oak Street Beach for some of the best accommodations and flight deals.

FAQs about cheap Oak Street Beach packages:

How to get cheap vacation deals to Oak Street Beach?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $115.

How much are Oak Street Beach packages?

Vacation packages to Oak Street Beach vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $293.

How to find cheap car rentals near Oak Street Beach?

Hotwire partners with some of the most reliable car rental companies in Downtown Chicago to bring you the best car rental deals in Oak Street Beach for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Oak Street Beach now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Oak Street Beach right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.