Near North Side Holidays

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Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Price was €765, price is now €572 per person
€572
per person
10 Nov - 16 Nov
found 1 day ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,980 reviews)
Extravagantly friendly staff, nice rooms with art deco touches, easy walk to a bunch of things, and to public transit. Have at least one dinner at the restaurant (Adamus) because the cod and the short rib tacos were Amazing! Also the tropical mocktail was so good i had three.

Reviewed on 9 Oct 2025

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,196, price is now €818 per person
€818
per person
10 Nov - 16 Nov
found 1 day ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,035 reviews)
The only things I didn’t care for was the unexpected $129 charge when checking in. Destination fee? Like I didn’t pay enough for the room, I get charged an extra fee that was not disclosed while booking. I wouldn’t have stayed there if I knew there was a “destination” fee. They gave us a $15 food credit. The breakfast was $30 a plate so pretty much a useless credit. The room was nice, however, I will not be returning to this hotel.

Reviewed on 5 Oct 2025

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was €805, price is now €582 per person
€582
per person
10 Nov - 16 Nov
found 1 day ago
Return flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,705 reviews)
The hotel needs to revise its description on various travel internet sites to indicate it no longer has an operating coffee bar. Also, it needs to clarify that the restaurant only serves breakfast and brunch on the weekends.

Reviewed on 9 Oct 2025

21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
Downtown Chicago
Price was €956, price is now €697 per person
€697
per person
10 Nov - 16 Nov
found 1 day ago
Return flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,626 reviews)
We had a wonderful stay at the 21c museum hotel! I wish it was for longer than one night. Clean, convenient to everything, comfy bed (very important), nice, hot shower with good water pressure (important) and friendly, kind staff. Highly recommend for anyone staying in Chicago!!

Reviewed on 8 Oct 2025

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
Price was €1,031, price is now €778 per person
€778
per person
10 Nov - 16 Nov
found 1 day ago
Return flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,691 reviews)
Only thing is having to pay for parking since the hotel doesn't have their own parking.

Reviewed on 7 Oct 2025

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 which includes a city

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

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 €167 per night from 9 Nov to 10 Nov
€167
9 Nov - 10 Nov
includes taxes & fees
8.4/10 Very Good! (5,052 reviews)
"good"

Reviewed on 7 Oct 2025

Embassy Suites by Hilton Chicago Downtown River North
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 €146 per night from 9 Nov to 10 Nov
€146
9 Nov - 10 Nov
includes taxes & fees
8.8/10 Excellent! (3,034 reviews)
"Awesome hotel. Super nice staff!"

Reviewed on 6 Oct 2025

Hilton Chicago/Magnificent Mile Suites
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €172 per night from 30 Oct to 31 Oct
€172
30 Oct - 31 Oct
includes taxes & fees
8.4/10 Very Good! (4,040 reviews)
"Rooms are clean, public transportation is close by and there is a lot of walkable food options."

Reviewed on 6 Oct 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 1,072 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 €572, 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.

Popular places to visit

Navy Pier

Navy Pier

4/5(125 reviews)

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

Navy Pier
Water Tower Place

Water Tower Place

4/5(24 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(84 reviews)

You can find out about the history of Chicago when you stop by John Hancock Center. Amble around this vibrant area's lakeside or experience its fascinating museums.

875 North Michigan Avenue

Things to do

Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

€38
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€38
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€38
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.