Old Town Chicago Vacation Packages 2025 from $224

Old Town Chicago flight + hotel vacation packages

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

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Save 100% on your flight

per person

Aug 5 - Aug 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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.

Kimpton Gray Hotel by IHG

Downtown Chicago

Save 100% on your flight

per person

Aug 5 - Aug 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. A hair salon, WiFi in public areas, and luggage storage are also on offer.

Eurostars Magnificent Mile

Downtown Chicago

Save 100% on your flight

per person

Jul 9 - Jul 15

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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

Downtown Chicago

per person

Aug 5 - Aug 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 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 lobby fireplace, a communal living room, and express check-out are also on offer.

Hilton Garden Inn Hoffman Estates

Save 100% on your flight

per person

Jul 30 - Aug 4

found 12 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a lobby fireplace are also on offer.

Top Old Town Chicago hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$215 nightly

$252 total

Jun 15 - Jun 16

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

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$211 nightly

$247 total

Jun 22 - Jun 23

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

Warwick Allerton - Chicago

701 North Michigan Avenue, Chicago, IL

$149 nightly

$175 total

Jun 4 - Jun 5

Total includes taxes and fees

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-out, and valet parking.

Air conditioning

Gym

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$167 nightly

$196 total

Jun 3 - Jun 4

Total includes taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A coffee shop, a snack bar/deli, and a lobby fireplace are also on offer.

Pet friendly

Free WiFi

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$173 nightly

$204 total

Jun 4 - Jun 5

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

Fairmont Chicago at Millennium Park

200 North Columbus Drive, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$264 nightly

$310 total

Jun 28 - Jun 29

Total includes taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Spa

Pet friendly

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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 fascinating museums.

Lighthouse ArtSpace Chicago

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

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 lively bars.

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 $224. 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.