Old Town Chicago Vacation Packages

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Flight and hotel packages to Old Town Chicago

Price found within the past 48 hours. Click for updated prices.
The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 11 - Jun 16
Roundtrip flight included
Newark (EWR) to Chicago (ORD)
This hotel features a gym and a steam room. Self parking, a 24-hour business center, and a coffee shop are also offered.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 11 - Jun 16
Roundtrip flight included
Newark (EWR) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, a snack bar/deli, and a free grocery shopping service are also on offer.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
per person
Jun 28 - Jun 30
Roundtrip flight included
Newark (EWR) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 24
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Dry cleaning and a safe deposit box are also provided.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 15 - Jul 19
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

Top Old Town Chicago hotel deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $159 per night
$159
per night
May 13 - May 14
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Breakfast available
Parking available
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $169 per night
$169
per night
May 12 - May 13
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.
Pet friendly
Parking available
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $140 per night
$140
per night
May 15 - May 16
This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking.
Pet friendly
Parking available
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $170 per night
$170
per night
May 12 - May 13
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $118 per night
$118
per night
May 27 - May 28
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and a communal living room are also offered.
Pet friendly
Parking available
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $116 per night
$116
per night
May 9 - May 10
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Valet parking, a business center, and a snack bar/deli are also offered.
Pet friendly
Breakfast available
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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.

Popular places to visit in Old Town Chicago

Image for Second City

Second City

4.5/5(10 reviews)

You can enjoy a show at Second City during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Second City
Image for Lighthouse ArtSpace Chicago

Lighthouse ArtSpace Chicago

You can spend time studying the exhibits at Lighthouse ArtSpace Chicago during your trip to Chicago. Discover the entertainment choices and notable monuments in this vibrant area.

Lighthouse ArtSpace Chicago
Image for Hudson Chess Park

Hudson Chess Park

Explore the great outdoors at Hudson Chess Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

Hudson Chess Park

Frequently asked questions

How much are vacation packages to Old Town Chicago?
Get ready to be surprised — you can vacation in Old Town Chicago for as low as $496. At Travelocity, we save you time and money with our vacation packages. With flights, hotels and tours all available at our one-stop shop, why wait any longer?
Where can I get the best vacation package deals for Old Town Chicago?
Scoring an unbeatable package deal to Old Town Chicago is a breeze with Travelocity. With access to 400 airlines and 1,000,000 properties around the world, you’re spoiled for choice when selecting your hotels and flights.
Why should I purchase my Old Town Chicago vacation bundle with Travelocity?
With exceptional service, 24/7 support and some of the most idyllic getaways on offer, you’ll never wander alone. And if you find a better price, we’ll match it. That’s our Price Match Guarantee.
Can I save money on my Old Town Chicago car rental if I book it with my hotel or flight?
Booking an Old Town Chicago vacation package with Travelocity is a simple way to save you time and money. You can bundle a flight, car and hotel, or any combination of them, and score great discounts. You can also throw in experiences and tours. After you’ve collected the keys to the rental car, head out of the neighborhood and discover what the surrounding area has to offer. Roughly 35 mi from Old Town Chicago, Six Flags Great America justifies a road trip.
What is the best time of year to go to Old Town Chicago?
You’ll nab the lowest hotel prices around and pay the most during . It’s generally quieter in January, September and December, while you’ll find many more fellow visitors to meet during March, April and June. It comes down to what prices you’re willing to pay, the climate and how well you handle crowds.