Near North Side Holidays

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Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €1,460, price is now €1,066 per person
€1,066
per person
8 Sept - 13 Sept
found 1 day ago
Return direct flight included
Stockholm (ARN) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on 8 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,340, price is now €1,538 per person
€1,538
per person
12 Sept - 17 Sept
found 1 day ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Wonderful amenities, clean and great location. The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.

Reviewed on 6 Jul 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,978, price is now €1,383 per person
€1,383
per person
12 Sept - 17 Sept
found 1 day ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,317, price is now €1,621 per person
€1,621
per person
8 Sept - 13 Sept
found 1 day ago
Return direct flight included
Warsaw (WAW) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
Excellent service. Room was fantastic with an incredible view of the city. Definitely worth every penny! Will go back for sure!

Reviewed on 9 Jul 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,201, price is now €1,559 per person
€1,559
per person
12 Sept - 17 Sept
found 1 day ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!

Reviewed on 8 Jul 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
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 Near North Side

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 €253 per night from 9 Aug to 10 Aug
€253
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (1,886 reviews)
"The room was amazing! It was spacious and clean. The staff were helpful and very considerate. The hotel is located in an ideal location, right off of Michigan Avenue, in the heart of downtown. Shopping and restaurants are within short walking distances."

Reviewed on 8 Jul 2026

Omni Chicago Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is €160 per night from 27 Jul to 28 Jul
€160
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,720 reviews)
"Great time"

Reviewed on 9 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 €201 per night from 9 Aug to 10 Aug
€201
9 Aug - 10 Aug
includes taxes & fees
9/10 Wonderful! (4,534 reviews)
"The suites are spacious and accommodated me, my husband, and mother in the same hotel room. She slept on the sofa bed and us in the bedroom with the door closed. We all had privacy. The hotel staff ate super friiendly and helpful. It is also close to Michigan Ave but is a walk to the river."

Reviewed on 9 Jul 2026

Hilton Chicago/Magnificent Mile Suites
See all 1,013 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 holiday package cost?
Starting from only €1,066, 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 holiday package. It's that simple! From hotels and flights to rental cars and tours, Expedia makes travelling 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?
Holiday Makers 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 holiday?
Travellers 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 holiday. 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 holiday package lets you organise your escape your way. Plus, you'll get access to great discounts when you combine your accommodation 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 holiday 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 holiday.
If I'm not able to travel, can I cancel my Near North Side holiday 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 holiday 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.

Stay near popular Near North Side attractions

A castle-like structure with turrets and a modern skyscraper in the background.

Water Tower Place

9.0/10 (1,113 reviews)
Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.