Oakland Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was S$908, price is now S$611 per person
S$611
per person
20 Sept - 23 Sept
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Our room this time was more cozy (re: small). Bathroom was efficient (re: cramped). I would guess they took a suite and made an extra room of it. Staff was great, hotel clean. Just a bad draw in the room - we arrived late.

Reviewed on 27 Jun, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,264, price is now S$850 per person
S$850
per person
20 Sept - 23 Sept
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
Best location on Michigan Avenue

Reviewed on 27 Jun, 2026

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was S$973, price is now S$684 per person
S$684
per person
20 Sept - 23 Sept
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very good! (3,950 reviews)
The Whitehall is “my Go To” when I am traveling solo, or with a girlfriend! Location is best in the city, for high end shopping and restaurants! Lake Michigan and Oak Street Beach are a “stones throw” away. This is one of the Real Classic Hotels. It is a bit dated, yet; all of my needs are met, with awesome beds, crisp clean linens, luggage racks, a safe for your valuables, along with marble bathrooms, really Hot Showers! The staff is always polite and helpful. The rooms are spacious and views can be awesome!😎 As a 25 year Chicagoan, whom no longer lives here, I Love 💕 this place… 👏 👏 👏

Reviewed on 26 Jun, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,152, price is now S$820 per person
S$820
per person
20 Sept - 23 Sept
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
Views were amazing on the water with a bonus fireworks show. Thanks Sable!

Reviewed on 26 Jun, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,315, price is now S$964 per person
S$964
per person
20 Sept - 23 Sept
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (2,201 reviews)
Clean room but the facilities are relatively outdated.

Reviewed on 27 Jun, 2026

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Top hotels in Oakland

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$210 per night from 30 Jun to 1 Jul
S$210
30 Jun - 1 Jul
includes taxes & fees
8/10 Very good! (10,138 reviews)
"4 days of a cold shower and a broken bed. I will never stay here again and I suggest that anyone thinking about staying here to look elsewhere. Bathrooms were severely outdated."

Reviewed on 27 Jun, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$278 per night from 5 Jul to 6 Jul
S$278
5 Jul - 6 Jul
includes taxes & fees
9.2/10 Wonderful! (1,828 reviews)
"Best location on Michigan Avenue"

Reviewed on 27 Jun, 2026

Omni Chicago Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$259 per night from 6 Jul to 7 Jul
S$259
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (4,467 reviews)
"The housekeeper was always so friendly and did such a great job. Honestly, all the staff was fantastic and so helpful."

Reviewed on 27 Jun, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,618 properties in Oakland
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.

Frequently asked questions

How much does an Oakland holiday package cost?
Customize your Oakland package from an affordable S$611. Choose from any combination of hotels, flights and rental cars to build the escape of your dreams. Remember to add on a few activities!
How do I get a cheap travel package to Oakland?
Bundle, bundle, bundle. Flights, rental cars and hotels — combine whatever you need into an Oakland holiday package to save loads of cash. Score even better deals when you add extras such as tours or experiences to your booking. But that's not the only good part. You have the freedom to customize your holiday your way. We offer more than 550 partner airlines and 1,000,000 hotel options all over the world, so that everyone has a chance to travel and fulfil those holiday fantasies.
Where should I stay in Oakland?
Most visitors to Oakland include University of Chicago and Chicago Museum of Science and Industry on their bucket lists. Why not go for a hotel close to one of these great attractions?
How far in advance should I book my Oakland holiday?
It's tricky picking the ideal time for airfares, but we usually say the earlier, the better. Many international flights on Expedia become available to compare up to 12 months in advance. If you're unable to do so, don't despair. Cheap prices appear from time to time within a few weeks of departure dates.
What does an Expedia Oakland travel package include?
Flights, car rentals and hotels — we bring you the best deals. All you have to do is select your preferred combination. After you've made your booking, you can add on the fun stuff like activities and tours. Our travel packages make it simple to craft an exciting Oakland holiday.
What should I know before booking an Oakland travel package?
You'll land impressive savings when you bundle your hotels, flights and rental cars into a package. Not only that, booking everything together makes trip planning much easier. So why waste time or money? Whether you're organising a fancy romantic getaway or a budget solo adventure, check out our holiday packages today.
Can I choose my airline with an Oakland Expedia holiday package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Just select the airline you want and create the perfect Oakland holiday.
If I'm not able to travel, can I cancel my Oakland holiday package?
It's hard to predict what the future holds, so it's good to know that you can change or cancel your Oakland holiday package. If your booking was made in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Stay near popular Oakland attractions

41st Street Beach

Why not spend a lazy afternoon at 41st Street Beach during your trip to Chicago? Stroll along the beaches or visit the shops while you're in the area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

S$52
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$31
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.