Near North Side Vacations from ￥59,669

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The Latest Near North Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
Price was ￥78,038, price is now ￥59,669 per person
￥59,669
per person
May 23 - May 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (2,820 reviews)
The breakfast was fresh and tasty, the only desire was flavored creamer options for my coffee.Rooms are clean and security felt great.

Reviewed on Apr 21, 2026

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥103,116, price is now ￥73,993 per person
￥73,993
per person
May 23 - May 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (1,006 reviews)
The rooms are nice. I was a little disappointed to find out there would be a hold of 80 dollars each day on a credit card

Reviewed on Apr 14, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥532,632, price is now ￥386,850 per person
￥386,850
per person
Jun 10 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.2/10 Wonderful! (449 reviews)
Everything was amazing from the staff to the amenities, the view and the cleanliness! I will definitely be booking again!

Reviewed on Apr 20, 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ￥86,567, price is now ￥65,850 per person
￥65,850
per person
May 23 - May 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
8.4/10 Very Good! (2,276 reviews)
Stayed for one night after returning from Europe. Check-in was easy and staff were very friendly. Great service at the restaurant and a decent gym. The carpet throughout the hotel, especially in the rooms, is in dire need of replacement. The carpet in my room must be 25 years old and filthy. The carpet was buckling in many places.

Reviewed on Apr 20, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥376,538, price is now ￥290,580 per person
￥290,580
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,831 reviews)
Excellent, customer service. Excellent, customer service excellent room excellent breakfast excellent rooftop excellent lounging area top-tier hotel.

Reviewed on Apr 20, 2026

Where to stay in Near North Side

Find the best Near North Side areas and neighborhoods for the activities you enjoy most. Learn more about Near North Side
Downtown Chicago

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

Near North Side Hotel Deals

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 ￥13,781 per night from Apr 26 to Apr 27
￥13,781
￥21,026 total
Apr 26 - Apr 27
includes taxes & fees
8.2/10 Very Good! (2,636 reviews)
The room was actually pretty good and pretty good size for two people and a queen bed I really loved it and I would go back again.

Reviewed on Apr 21, 2026

Hotel Felix River North/Magnificent Mile
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,434 per night from Apr 26 to Apr 27
￥21,434
￥29,637 total
Apr 26 - Apr 27
includes taxes & fees
9.4/10 Exceptional! (3,910 reviews)
Excellent, customer service. Excellent, customer service excellent room excellent breakfast excellent rooftop excellent lounging area top-tier hotel.

Reviewed on Apr 20, 2026

Hotel Riu Plaza Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥26,832 per night from Apr 26 to Apr 27
￥26,832
￥31,501 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (5,864 reviews)
What a fantastic hotel. Walking distance to so much of downtown. The staff were polite and helpful, the room was great! My wife says “this is where we are staying when we come to Chicago from now on.”

Reviewed on Apr 21, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 1,043 properties in Near North Side
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 Near North Side vacation package cost?
Starting from only ￥59,669, a package is your passport to low-cost travel. Put together your Near North Side trip by picking from our wide range of hotels, airfares and rental cars.
How do I get a cheap travel package to Near North Side?
Secure flights that fit in with your schedule, add a hotel to your booking and watch the savings rack up with a Near North Side vacation package. It's that simple! From hotels and flights to rental cars and tours, Expedia makes traveling cheaply a cinch. And with more than 550 partner airlines and 1,000,000 properties throughout the world to choose from, you'll never be short of choice.
Where should I stay in Near North Side?
Vacationers come from all over to see McCormick Place and Millennium Park in Near North Side. Book a room near these awesome attractions and visit them whenever you please.
What are the top hotels in Near North Side?
Sable at Navy Pier Chicago, Curio Collection by Hilton and Kasa River North Chicago are a couple of the most well-known properties in Near North Side. Why not take a look at the facilities and rates at each and then decide?
How far in advance should I book my Near North Side vacation?
Travelers can normally compare international flights on Expedia within 12 months of departure. Booking late? With a stroke of luck, it's still possible to score a cheaper ticket only weeks before your journey.
What does an Expedia Near North Side travel package include?
Travel packages include hotels, rental cars and flights, but you can mix and match them to create your perfect Near North Side vacation. You can also add on a few activities and tours once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll score deals you won't find elsewhere.
What should I know before booking a Near North Side travel package?
Whether it's relaxation or adventure you're seeking, a Near North Side vacation package lets you organize your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Near North Side Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you sure can! Simply pick the carrier you want and create your ideal Near North Side vacation.
If I'm not able to travel, can I cancel my Near North Side vacation package?
Yes, you can. We get that even the best-laid plans can go awry, so we're here to help if you need to make changes to your Near North Side vacation package. You may be able to cancel or amend your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Near North Side

Merchandise Mart

Merchandise Mart

4.5/5(340 reviews)

You can learn about the history of Chicago with a trip to Merchandise Mart. Amble around this vibrant area's riverfront or experience its entertainment choices.

Merchandise Mart
Water Tower Place

Water Tower Place

4.5/5(845 reviews)

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Water Tower Place
875 North Michigan Avenue

875 North Michigan Avenue

4.5/5(1,936 reviews)

You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

875 North Michigan Avenue

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,285
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,982
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,348
per adult
94% of travellers recommend
Art Institute of Chicago
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.