Old Town Chicago Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Old Town Chicago

Find the best Old Town Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Chicago
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in Old Town Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is 3.247.722 ₫ per night from 26 Apr to 27 Apr
3.247.722 ₫
3.812.729 ₫ total
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,142 reviews)
My friend was given a very small room and never got room service. Also, we want adjoining rooms, which they could not give us but put us on the same floor as far apart as was possible. I had requested the adjoining rooms with Expedia long before we arrived. Obviously, you have no clout with them. ...

Reviewed on 14 Apr 2026

Congress Plaza Hotel
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 3.630.442 ₫ per night from 26 Apr to 27 Apr
3.630.442 ₫
4.262.031 ₫ total
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (4,131 reviews)
Hotel was close to the Mile and attractions. Facilities in good condition, somewhat aged, Do no expect an impressive an inviting Lobby and Lounge. Side Bar was expensive for what it offered. Space was clean and staff attentive. Suite was of OK dimensions. Room TV's were old but functional. Shower ...

Reviewed on 14 Apr 2026

Hilton Chicago/Magnificent Mile Suites
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
The price is 4.095.343 ₫ per night from 26 Apr to 27 Apr
4.095.343 ₫
4.807.577 ₫ total
26 Apr - 27 Apr
includes taxes & fees
8.6/10 Excellent! (5,836 reviews)
Clean, friendly staffs, good service. Love happy hours with drinks and appetizers, breakfast service is awesome.

Reviewed on 13 Apr 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,674 properties in Old Town Chicago
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 an Old Town Chicago holiday package cost?
Maybe less than you might think — from just , in fact! By bundling flights, hotels and car rentals into a tailor-made package, your Old Town Chicago escape is just a few clicks away.
How do I get a cheap travel package to Old Town Chicago?
Just think of all the fun things you could do in Old Town Chicago with a wad of extra cash in your pocket. Watch your savings stack up when you bundle your flights, hotels and extras into an Old Town Chicago holiday package. You have loads of choice when you book your trip with Expedia too. In fact, you can pick from more than 550 airlines and 1null000null000 properties worldwide. Whether you're heading away with the whole family or surprising your special someone, organising a getaway to Old Town Chicago is better with a package.
Where should I stay in Old Town Chicago?
Take the hassle out of sightseeing by staying someplace close to Old Town Chicago's iconic attractions. Wrigley Field and Lincoln Park Zoo are two of the most popular.
What are the top hotels in Old Town Chicago?
The Sono Chicago and Hotel Lincoln, part of JdV by Hyatt are among the most well-known properties in Old Town Chicago. Why not look up the rates and facilities at each and then decide?
How far in advance should I book my Old Town Chicago holiday?
While prices change frequently, we generally recommend booking your holiday as soon as possible. Most international airfares are available on Expedia up to a year in advance. If circumstances have left you booking late, you might still be in luck. Cheap journeys to Old Town Chicago sometimes emerge only weeks before departure.
What does an Expedia Old Town Chicago travel package include?
Hotels, flights and rental cars, or any combination of the three — you decide! Whether you're exploring Old Town Chicago with the kids or adventuring solo, there's a package to fit every style and budget. Once you've made your booking, why not add on a couple of tours and experiences?
What should I know before booking an Old Town Chicago travel package?
You'll score impressive savings when you combine your flights, hotels and rental cars into a travel package. Plus, booking everything in one spot just makes things easier. So why waste your money or time? Whether you're putting together a luxury city stay with your love or a budget solo adventure, browse our holiday packages today.
Can I choose my airline with an Old Town Chicago Expedia holiday package?
With a holiday package, you're the one in charge. Whether you're eager to fly to Old Town Chicago in economy or business class, simply choose from the available airline options. Expedia has access to more than 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Old Town Chicago holiday package?
Because we understand life can throw you a few curveballs, the answer is yes. For further details, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it with no penalties. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.

Popular places to visit

Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

5/5(1 review)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
McCormick Place

McCormick Place

4.5/5(36 reviews)

During your trip, find out what's happening in McCormick Place, a top convention centre in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.

McCormick Place