Near North Side Holidays from £473

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Your Near North Side Holiday

Discover all the amazing things this neighbourhood has to offer with a customized Near North Side holiday package. However you imagine yourself spending your time here, you'll find countless opportunities for fun, relaxation and adventure. Some popular nearby attractions to visit during your trip to Near North Side include Millennium Park, Willis Tower and Art Institute of Chicago. Stop dreaming and start doing. When it's time to lock in your holiday to Near North Side, Expedia will help get you there.

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £711, price is now £473 per person
£473
per person
3 Oct - 7 Oct
found 1 day ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,825 reviews)
Staying here was nothing short of amazing thanks to this staff. They were very friendly, courteous and nice. Everyone was attentive and you can tell. They really loved working there and delivering service.

Reviewed on 20 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,928, price is now £1,124 per person
£1,124
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,488, price is now £956 per person
£956
per person
13 Nov - 17 Nov
found 24 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,670, price is now £1,090 per person
£1,090
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
Hotel is located very centric. Nice view very quiet

Reviewed on 22 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,097, price is now £1,394 per person
£1,394
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Staff was amazing!! Everything was so easy checking in and checking out. The stay was great! It was so nice having the pier to ourselves after hours.

Reviewed on 20 Aug 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 featuring 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

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £131 per night from 1 Sept to 2 Sept
£131
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 20 Aug 2025

The Wade
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 £132 per night from 3 Sept to 4 Sept
£132
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,752 reviews)
"Great location. Nice size rooms. Breakfast was really good, only way to busy and crowded during that experience. They should extend the breakfast hours by an hour to reduce the over crowding. Overall good stay. Would return.."

Reviewed on 23 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
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 £124 per night from 2 Sept to 3 Sept
£124
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (3,738 reviews)
"Good 👍"

Reviewed on 23 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 1,148 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Near North Side travel package cost?
Starting from a low £473, a travel package is your ticket to low-cost travel. Put together your Near North Side adventure by selecting from our extensive range of airfares, hotels and rental cars.
If I'm not able to travel, can I cancel my Near North Side travel package?
We totally understand — life can throw you the odd curveball. If you've locked in a Near North Side travel package and need to amend or cancel it, we're here to help. It's always worth visiting our Customer Service Portal first for information. But generally, if you've taken out your package in the last 24 hours, you may be able to change your itinerary at no cost. If it's been longer than 24 hours, your hotel, airline or car rental company may impose a fee.
How do I get a cheap travel package to Near North Side?
Browse and lock in everything in the one place with our Near North Side travel packages. We have incredible bargains on flights, hotels and more that'll keep your bank account happy and your adventurousness alive. And, with more than 550 airlines and 1,000,000 properties across the globe to choose from, there are endless opportunities to mix and match your own way.
Does Expedia offer Book Now, Pay Later Near North Side holidays?
Your bank balance shouldn't stop you from going on holiday, so Expedia has come up with a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book an incredible getaway without hurting your hip pocket. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: Klarna has manageable monthly payment plans that work for all budget sizes, so you can take that well-deserved holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your holiday across multiple transactions.
  • Low deposit holidays: Hitting the "book now" button is easier with this payment plan. Put down a small deposit on your booking and then start working on your travel itinerary.

Where should I stay in Near North Side?
Urban adventurers come from all over the world to experience Millennium Park and Wrigley Field in Near North Side. Book a hotel within a stone's throw of these awesome attractions and visit them whenever you want.
What are the top hotels in Near North Side?
Lock in a room at Hyatt Regency Chicago. It's one of the area's most sought-after hotels. Another great option in Near North Side is The Godfrey Hotel Chicago.
How far in advance should I book my Near North Side holiday?
It all depends on the airline, but you can generally look up international flights on Expedia up to 12 months in advance. While it's advisable to book ahead of time, lucky travellers will sometimes find a cheaper seat just weeks before departure dates.
What does an Expedia Near North Side travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your perfect Near North Side getaway. 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 get access to deals you won't find elsewhere.
What should I know before booking a Near North Side travel package?
So many places to explore, so many things to see. With a travel package, you'll be able to afford more of them. Bundle your hotels, flights and rental cars and get set to save.
Can I choose my airline with a Near North Side Expedia travel package?
You sure can. We offer more than 550 partner airlines throughout the world, so choose the carrier that best fits your budget and travelling style.

Popular places to visit

Navy Pier

Navy Pier

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

Navy Pier
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 theatre scene.

Merchandise Mart
John Hancock Center

John Hancock Center

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 acclaimed theatre scene.

John Hancock Center

Things to do

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

£31
per adult
88% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
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. Flight-inclusive packages are ATOL protected.