Old Town Chicago Vacation Packages 2025/2026 from $319

Old Town Chicago flight + hotel vacation packages

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

HYATT house Chicago/Schaumburg

Save 100% on your flight

per person

Sep 15 - Sep 20

found 21 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a sauna. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

The Wade

Downtown Chicago

per person

Aug 12 - Aug 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-in are also provided.

Park Hyatt Chicago

Downtown Chicago

per person

Aug 12 - Aug 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

The Langham, Chicago

Downtown Chicago

Save 100% on your flight

per person

Oct 2 - Oct 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and laundry facilities.

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

Save 100% on your flight

per person

Aug 12 - Aug 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.

Top Old Town Chicago hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$210 total

Jul 27 - Jul 28

Total includes taxes and fees

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.

Free WiFi

Restaurant

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave, Chicago, IL

$231 nightly

$266 total

Aug 10 - Aug 11

Total includes taxes and fees

This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.

Pool

Spa

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$151 nightly

$178 total

Aug 10 - Aug 11

Total includes taxes and fees

A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

Pet friendly

Free WiFi

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$211 nightly

$247 total

Jul 20 - Jul 21

Total includes taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.

Pool

Breakfast included

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street, Chicago, IL

Free Cancellation

$147 nightly

$173 total

Aug 10 - Aug 11

Total includes taxes and fees

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. Self parking, a coffee shop, and a snack bar/deli are also offered.

Pet friendly

Free WiFi

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

$165 nightly

$194 total

Aug 11 - Aug 12

Total includes taxes and fees

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. A coffee shop, a communal living room, and express check-in are also on offer.

Free WiFi

Restaurant

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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

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 entertainment choices.

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.

Henry Gerber House

Learn about the local history of Chicago with a stop at Henry Gerber House. Stroll along the lakeside or visit the shops in this vibrant area.

Frequently asked questions

How much are vacation packages to Old Town Chicago?

Treat yourself to an unforgettable travel experience in Old Town Chicago with a vacation package starting at just $319. Booking your tours, flights and hotels with Travelocity is a piece of cake. And even better, our vacation deals will leave you with more money in your pocket for fun times.

Where can I get the best vacation package deals for Old Town Chicago?

For a fun and affordable package deal to Old Town Chicago, nothing compares to Travelocity. Choose from 400 air carriers and 1,000,000 properties around the world to create the ideal escape --- it's really that easy.

Why should I book my Old Town Chicago vacation package via Travelocity?

Nothing beats the feeling of knowing you've bagged the best deal available --- that's our Price Match Guarantee. Add to that our enormous range of magical destinations and 24/7 team of customer service professionals and you've got the formula for a hassle-free vacation.

Can I save money on my Old Town Chicago car rental if I bundle it with hotels and flights?

Sure can --- and booking one of our Old Town Chicago vacation packages is the ideal way to do this. Bundle any combination of a hotel, flight, car and experience and score serious discounts. The more you book, the more you save. There are so many famous sights around Old Town Chicago that are worth a road trip, including Six Flags Great America (35 mi from Old Town Chicago). Nothing beats discovering thrilling places like this with the freedom of your own wheels.

What is there to do in Old Town Chicago?

Second City is an awesome place to start your sightseeing. Bring some comfy sneakers, because this neighborhood will keep you on the go.