Near North Side Holidays from £719

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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.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was £898, price is now £719 per person
£719
per person
20 Jan - 24 Jan
found 2 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Not worth it for the money. Good location but nothing special.

Reviewed on 8 Nov 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,797, price is now £1,324 per person
£1,324
per person
25 Dec - 30 Dec
found 1 hour ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,091, price is now £818 per person
£818
per person
20 Jan - 24 Jan
found 2 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on 8 Nov 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was £1,079, price is now £841 per person
£841
per person
11 Jan - 16 Jan
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £1,202, price is now £955 per person
£955
per person
20 Jan - 24 Jan
found 2 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,309 reviews)
Staff, per usual, went above and beyond. Phenomenal experience every single time. The terrace room, even on pricier days, is better than any other luxury hotel in the city.

Reviewed on 7 Nov 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

4 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 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 £103 per night from 11 Nov to 12 Nov
£103
11 Nov - 12 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
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 £106 per night from 23 Nov to 24 Nov
£106
23 Nov - 24 Nov
includes taxes & fees
8.6/10 Excellent! (2,197 reviews)
"The hotel wasn’t bad at all. Dakota at the front desk was awesome. Besides that, I did encounter some hiccups after checking in. The room wasn’t cleaned properly and some of the previous guest items were still in the room. Besides that the staff was good"

Reviewed on 8 Nov 2026

The Wade
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £93 per night from 9 Nov to 10 Nov
£93
9 Nov - 10 Nov
includes taxes & fees
The Chicago Hotel Collection - Magnificent Mile
See all 935 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 £719, 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.

Stay near popular Near North Side attractions

A large, historic building with a central tower and multiple windows, located near a body of water.

Merchandise Mart

8.6/10 (419 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 fascinating museums.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
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
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.