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Oak Street Beach Vacation Packages

Oak Street Beach Flight + Hotel Packages

Prices and availability subject to change. Additional terms may apply.
W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Stay at this luxury hotel in Chicago. Enjoy breakfast, WiFi, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby. Discover genuine guest reviews for W Chicago - Lakeshore, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
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
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, 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. Discover genuine guest reviews for Ambassador Chicago, part of JdV by Hyatt, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Sonesta ES Suites Chicago Waukegan Gurnee

Sonesta ES Suites Chicago Waukegan Gurnee

3 out of 5
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Waukegan. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Naval Base Great Lakes and Six Flags Great America are located nearby. Discover genuine guest reviews for Sonesta ES Suites Chicago Waukegan Gurnee along with the latest prices and availability – book now.
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and room service. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Omni Chicago Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Kimpton Gray Hotel, an IHG Hotel

Kimpton Gray Hotel, an IHG Hotel

4.5 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 24
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast, WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Willis Tower and Millennium Park are located nearby. Discover genuine guest reviews for Kimpton Gray Hotel, an IHG Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Chez Hotel Arlington Heights

Chez Hotel Arlington Heights

3.5 out of 5
per person
Jun 19 - Jun 23
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 3.5-star hotel in Arlington Heights. Enjoy free WiFi, free parking, and breakfast. Popular attractions LEGOLAND® Discovery Center and Woodfield Mall are located nearby. Discover genuine guest reviews for Chez Hotel Arlington Heights along with the latest prices and availability – book now.
AC Hotels by Marriott Chicago Downtown

AC Hotels by Marriott Chicago Downtown

4 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, 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. Discover genuine guest reviews for AC Hotels by Marriott Chicago Downtown, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Best Western Plus Chicagoland - Countryside

Best Western Plus Chicagoland - Countryside

3.5 out of 5
per person
Jun 14 - Jun 18
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this hotel in La Grange. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions SeatGeek Stadium and Park District of La Grange are located nearby. Discover genuine guest reviews for Best Western Plus Chicagoland - Countryside along with the latest prices and availability – book now.
Hampton Inn & Suites Chicago-Burr Ridge

Hampton Inn & Suites Chicago-Burr Ridge

2.5 out of 5
per person
Jun 14 - Jun 18
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this business-friendly hotel in Burr Ridge. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions SeatGeek Stadium and Burr Ridge Village Center are located nearby. Discover genuine guest reviews for Hampton Inn & Suites Chicago-Burr Ridge along with the latest prices and availability – book now.
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
per person
Jun 14 - Jun 18
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby. Discover genuine guest reviews for Country Inn & Suites by Radisson, Chicago O'Hare South, IL along with the latest prices and availability – book now.
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Stay at this business-friendly hotel in Chicago. Enjoy WiFi, a fitness center, and valet parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Hilton Chicago/Magnificent Mile Suites, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby. Discover genuine guest reviews for Le Méridien Essex Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.

3-4 Night Vacations in Oak Street Beach

Prices and availability subject to change. Additional terms may apply.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Jun 12 - Jun 15
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Jun 12 - Jun 15
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Kimpton Gray Hotel, an IHG Hotel

Kimpton Gray Hotel, an IHG Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 20 - Jun 24
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)

5-7 Night Vacations in Oak Street Beach

Prices and availability subject to change. Additional terms may apply.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Orlando (MCO) to Chicago (ORD)

Oak Street Beach Last Minute Hotel Deals

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 a 24-hour health club, onsite parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Hotel Felix River North/Magnificent Mile
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
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 ...
Congress Plaza Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
The Westin Michigan Avenue Chicago
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Stay at this business-friendly hotel in Chicago. Enjoy WiFi, a fitness center, and valet parking. Our guests praise the pool and the helpful staff in our reviews. ...
Hilton Chicago/Magnificent Mile Suites
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
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
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3 out of 5
243 E. Ontario, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular ...
Aloft Chicago Mag 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, and onsite parking. Our guests praise the helpful staff and the clean rooms in our ...
The Whitehall Hotel, BW Premier Collection
See all 3,611 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 $341.

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 $82.

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 $341.

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.

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