Near North Side Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Jul 9 - Jul 20

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    11 nights
    4.0 star property
    8.2/10 - Very Good (2,758 reviews)
    "The staff were friendly and helpful."
    Reviewed June 5, 2026
    Roundtrip • Tokyo (HND) - Chicago (ORD)
    HND - ORD • 1 stop ORD - NRT • 1 stop
    ￥664,976
    ￥515,076
    per traveler
    found 20 hours ago
    Hotel Felix River North/Magnificent Mile
  • Front of property
    Jul 9 - Jul 20

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    11 nights
    4.0 star property
    9.4/10 - Exceptional (4,353 reviews)
    "The only complaint I have is the TV in the room, hard to navigate"
    Reviewed June 5, 2026
    Roundtrip • Tokyo (HND) - Chicago (ORD)
    HND - ORD • 1 stop ORD - NRT • 1 stop
    ￥788,655
    ￥547,408
    per traveler
    found 20 hours ago
    Hotel Riu Plaza Chicago
  • Breakfast and dinner served
    Jul 9 - Jul 20

    Omni Chicago Hotel + Flight

    Downtown Chicago
    11 nights
    4.5 star property
    9.2/10 - Wonderful (1,789 reviews)
    "Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too."
    Reviewed June 3, 2026
    Roundtrip • Tokyo (HND) - Chicago (ORD)
    HND - ORD • 1 stop ORD - NRT • 1 stop
    ￥658,901
    ￥526,351
    per traveler
    found 20 hours ago
    Omni Chicago Hotel
  • Reception hall
    Jul 9 - Jul 20

    Eurostars Magnificent Mile + Flight

    Downtown Chicago
    11 nights
    4.0 star property
    9.0/10 - Wonderful (3,607 reviews)
    "Had an amazing stay here!"
    Reviewed June 5, 2026
    Roundtrip • Tokyo (HND) - Chicago (ORD)
    HND - ORD • 1 stop ORD - NRT • 1 stop
    ￥639,677
    ￥522,158
    per traveler
    found 20 hours ago
    Eurostars Magnificent Mile
  • Exterior
    Jul 9 - Jul 20

    Arlo Chicago + Flight

    Downtown Chicago
    11 nights
    4.0 star property
    9.4/10 - Exceptional (2,125 reviews)
    "Amazing experience and excellent location!"
    Reviewed June 5, 2026
    Roundtrip • Tokyo (HND) - Chicago (ORD)
    HND - ORD • 1 stop ORD - NRT • 1 stop
    ￥673,159
    ￥557,585
    per traveler
    found 20 hours ago
    Arlo Chicago

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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is ￥24,305 per night from Jun 28 to Jun 29
￥24,305
￥28,896 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,520 reviews)
"👍"

Reviewed on Jun 5, 2026

The Chicago Hotel Collection - 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 ￥30,243 per night from Jun 30 to Jul 1
￥30,243
￥40,517 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,353 reviews)
"The only complaint I have is the TV in the room, hard to navigate"

Reviewed on Jun 5, 2026

Hotel Riu Plaza Chicago
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Fully refundable
The price is ￥29,442 per night from Jun 28 to Jun 29
￥29,442
￥35,004 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,358 reviews)
"Check in was delayed, said they would text when room was ready but never did"

Reviewed on May 31, 2026

Holiday Inn Chicago Dwtn - The Mart by IHG
See all 1,021 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 , 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

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

Merchandise Mart
Water Tower Place

Water Tower Place

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

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

￥4,236
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,904
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,276
per adult
92% 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.