Downtown Chicago Vacations from ₩974,474

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The Latest Downtown Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
Forest Glen
Price was ₩1,134,837, price is now ₩974,474 per person
₩974,474
per person
May 19 - May 24
found 14 hours ago
Roundtrip flight included
Orange County (SNA) to Chicago (ORD)
6.6/10 (416 reviews)
it’s pretty nice to stay , i will still recommend more people trust me

Reviewed on Mar 28, 2026

Wyndham Garden Elk Grove Village/O'Hare

Wyndham Garden Elk Grove Village/O'Hare

3 out of 5
Price was ₩1,232,587, price is now ₩1,049,582 per person
₩1,049,582
per person
May 19 - May 24
found 14 hours ago
Roundtrip flight included
Orange County (SNA) to Chicago (ORD)
8.6/10 Excellent! (1,013 reviews)
Basic hotel, was great for our need.

Reviewed on Apr 17, 2026

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

4 out of 5
Price was ₩1,382,485, price is now ₩1,210,265 per person
₩1,210,265
per person
May 19 - May 24
found 14 hours ago
Roundtrip flight included
Orange County (SNA) to Chicago (ORD)
8.6/10 Excellent! (1,006 reviews)
Clean king size bed but the full double beds I had at first had an a/c problem

Reviewed on Apr 16, 2026

Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Price was ₩1,640,680, price is now ₩1,439,282 per person
₩1,439,282
per person
May 19 - May 24
found 14 hours ago
Roundtrip flight included
Orange County (SNA) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
Everything was great during our stay

Reviewed on Apr 12, 2026

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
Price was ₩1,619,872, price is now ₩1,422,638 per person
₩1,422,638
per person
May 19 - May 24
found 14 hours ago
Roundtrip flight included
Orange County (SNA) to Chicago (ORD)
8.8/10 Excellent! (2,497 reviews)
Very convenient for travelers arriving late at O’Hare. The shuttle drivers are friendly and helpful, which makes a stressful travel day much easier. With flight delays becoming the “new normal” at ORD, staying near the airport on the first night is a practical solution. The hotel also offers excellent access to public transit (e.g. CTA train) to downtown Chicago. The on‑site restaurant serves good food, making it easy to settle in without needing to go far.

Reviewed on Apr 18, 2026

Where to stay in Downtown Chicago

Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Chicago
Magnificent Mile

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Find hotels in Magnificent Mile

Downtown Chicago Hotel Deals

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 ₩168,049 per night from Apr 26 to Apr 27
₩168,049
₩197,283 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,142 reviews)
Our room was uncomfortably warm. They explained that the hotel is old and they put either the air conditioner on or the heat on in the hotel and since it was going to be cool the next day they had turned the heat on to begin heating the hotel for the next day. They did give us a fan and opened the ...

Reviewed on Apr 18, 2026

Congress Plaza Hotel
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩126,752 per night from Apr 26 to Apr 27
₩126,752
₩193,385 total
Apr 26 - Apr 27
includes taxes & fees
8.2/10 Very Good! (2,624 reviews)
I found the price you pay for breakfast inclusion there would be more options then a danish, fruit, yogurt, and a coffee that there is a limitation on how much you get. The room was clean, there was issues with plumbing but they were working on fixing it. On the second floor the walls are thin I ...

Reviewed on Apr 18, 2026

Hotel Felix River North/Magnificent Mile
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundable
The price is ₩184,944 per night from Apr 28 to Apr 29
₩184,944
₩217,129 total
Apr 28 - Apr 29
includes taxes & fees
8.8/10 Excellent! (3,430 reviews)
This is a janky hotel, but it is close to where all meetings are held.

Reviewed on Apr 17, 2026

Club Quarters Hotel, Central Loop, Chicago
See all 1,673 properties in Downtown Chicago
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 a Downtown Chicago vacation package cost?
Go from looking to booking with our Downtown Chicago vacation packages, which start from just ₩974,474. Handpick the hotels and flights that suit your travel style. Then, add on a couple of tours or activities for an amazing adventure.
How do I get a cheap travel package to Downtown Chicago?
Bundle your bookings with Expedia to save big on your next trip. With more than 550 partner airlines and 1,000,000 hotels across the world, your Downtown Chicago vacation package can be tailored exactly to suit your budget. With all that extra money, why not include one or two fun tours and activities? It's an easy way to unlock even more savings. The vacation you've always dreamed of in Downtown Chicago is much closer than you thought!
How far in advance should I book my Downtown Chicago vacation?
While not all airlines advertise tickets early, you can normally look up international airfares on Expedia up to 12 months in advance. This is the time you'll score some incredible deals. If you've left things to the last minute, you could still be in luck. Discounted prices occasionally emerge a few weeks before departure.
What does an Expedia Downtown Chicago travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your ideal Downtown Chicago trip. You can also add on fun things like activities and tours once you've made your booking. You're in charge! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Downtown Chicago travel package?
Our prices are always low. However, you'll pick up even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice.
Can I choose my airline with a Downtown Chicago Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You're in charge! We have more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Downtown Chicago trip.
If I'm not able to travel, can I cancel my Downtown Chicago vacation package?
You can. We understand that even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Downtown Chicago vacation package. You may be able to change or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Downtown Chicago

Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.