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Find 5 Star Hotels in Old Town Chicago, IL from $173

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Check availability on Old Town Chicago 5 Star Hotels

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Oct 3 - Oct 4
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Oct 4 - Oct 5
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Oct 3 - Oct 5
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Oct 10 - Oct 12

Compare Old Town Chicago 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Trump International Hotel & Tower Chicago
Bar (on property)

Trump International Hotel & Tower Chicago

5.0 star property
9.4 out of 10, Exceptional, (1731)
"Beautiful hotel centrally located"
$431 nightly
The price is $506
Nov 2 - Nov 3
Total with taxes and fees
Trump International Hotel & Tower Chicago
The Langham, Chicago
Lobby

The Langham, Chicago

5.0 star property
9.8 out of 10, Exceptional, (1001)
"Great place to stay. "
$544 nightly
The price is $638
Oct 26 - Oct 27
Total with taxes and fees
The Langham, Chicago
The Peninsula Chicago
Front of property - evening/night

The Peninsula Chicago

5.0 star property
9.8 out of 10, Exceptional, (1001)
"Amazing hotel will be back for sure!"
$625 nightly
The price is $734
Nov 2 - Nov 3
Total with taxes and fees
The Peninsula Chicago
Four Seasons Hotel Chicago
Reception

Four Seasons Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (1000)
"Amazing hotel"
$530 nightly
The price is $622
Nov 2 - Nov 3
Total with taxes and fees
Four Seasons Hotel Chicago
Waldorf Astoria Chicago
Exterior

Waldorf Astoria Chicago

5.0 star property
9.4 out of 10, Exceptional, (1000)
"Simply love this hotel"
$582 nightly
The price is $684
Nov 3 - Nov 4
Total with taxes and fees
Waldorf Astoria Chicago
Park Hyatt Chicago
Suite, Terrace (Water Tower) | 1 bedroom, premium bedding, down comforters, pillowtop beds

Park Hyatt Chicago

5.0 star property
9.6 out of 10, Exceptional, (1003)
"beautiful room and hotel great bar!"
$570 nightly
The price is $669
Nov 3 - Nov 4
Total with taxes and fees
Park Hyatt Chicago
Nobu Hotel Chicago
Indoor pool, open 6:00 AM to 9:00 PM, sun loungers

Nobu Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (729)
"Great location, amenities and staff. "
$525 nightly
The price is $616
Oct 30 - Oct 31
Total with taxes and fees
Nobu Hotel Chicago
The Ritz-Carlton, Chicago
Bar (on property)

The Ritz-Carlton, Chicago

5.0 star property
9.2 out of 10, Wonderful, (1001)
"Beautiful place "
$460 nightly
The price is $540
Nov 2 - Nov 3
Total with taxes and fees
The Ritz-Carlton, Chicago
The St. Regis Chicago
2 restaurants, breakfast served

The St. Regis Chicago

5.0 star property
9.2 out of 10, Wonderful, (77)
"Nice place "
$625 nightly
The price is $734
Oct 5 - Oct 6
Total with taxes and fees
The St. Regis Chicago
Art Villa
Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
$635 nightly
The price is $790
Oct 12 - Oct 13
Total with taxes and fees
Art Villa
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Old Town Chicago.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL
$189 nightly
The price is $221 total per night from Nov 3 to Nov 4
$221 total
Nov 3 - Nov 4
Total with taxes and fees
8.4/10 Very Good! (5,023 reviews)
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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.

Top Old Town Chicago Hotel Reviews

Find out more about Old Town Chicago

Find out more about Old Town Chicago

Why not request complete opulence on your trip to Old Town Chicago? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Old Town Chicago so popular in the last year. There's no reason to delay a getaway to Old Town Chicago any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Reserve one of our 5-star hotels in Old Town Chicago and indulge in the finer things in life for a while. Don't wait any longer!

Book the Best Old Town Chicago 5-Star Hotels

You'll have a wonderful time at one of these 5-star hotels. Highly-rated eateries, concierges, and pillow-fluffing are all at the ready. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. What creature comforts do you want in your lodging? 24-hour room service, so you can order that chocolate soufflé© in the wee hours of the morning? A mud wrap treatment that will leave you feeling like a million bucks? Butler services? No matter what you want on a perfect getaway, you're bound to find it here.

But you aren't going to spend your entire vacation in your room, of course. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Old Town Chicago are waiting for you to rest up after an exciting day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs.

Your Getaway Starts Today

The results are in, and Old Town Chicago 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. It's time to plan your next great escape -- Expedia can help you land a great deal on accommodation. Select one of Expedia's Old Town Chicago 5-star hotels today and decompress in the lap of luxury when you're ready.

Frequently asked questions

What are the best 5-star hotels in Old Town Chicago?
According to reviews by our customers, Waldorf Astoria Chicago is one of the leading retreats for an indulgent stay in the North Side neighborhood of Old Town Chicago. Looking for more 5-star hotels around the area? Four Seasons Hotel Chicago and Park Hyatt Chicago will meet your high-end needs.
How much does it cost to stay in a 5-star hotel in Old Town Chicago?
You can find various pricing options for 5-star hotels in Old Town Chicago on Expedia. How much you'll pay will depend on when you travel, length of stay and other factors. Compare all of the available accommodations for your preferred dates and use our pricing and other filters to score the perfect high-end stay.

  • Search for the lowest price per night from $173

What makes a hotel 5 stars in Old Town Chicago?
In Old Town Chicago, a hotel must offer a certain number of top-notch amenities to be rated 5 stars. These may include gourmet restaurants, on-site gyms, saunas and spas, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their guest-focused service. You can expect things like concierge services, in-room massages and nightly turn-down services. Some may also offer extra touches such as welcome gifts.

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Explore a world of travel with Expedia