Chicago Vacation Packages 2025 from $348

Chicago flight + hotel vacation packages

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

Hampton Inn & Suites Addison

per person

Jul 4 - Jul 6

found 11 hours ago

Roundtrip flight included

New York (NYC) to Chicago (ORD)

This hotel features an indoor pool and a gym. 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.

Howard Johnson by Wyndham Merrillville

per person

Jun 3 - Jun 9

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) 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. Guests will appreciate freebies like continental breakfast and free self parking.

LakeWood Inn & Suites

per person

Jun 5 - Jun 8

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the laundry service. Luggage storage is provided and the front desk is staffed around-the-clock.

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Save 100% on your flight

per person

Jul 6 - Jul 11

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 15 conference rooms on site, along with the valet parking and WiFi in public areas. Self parking, a lobby fireplace, and luggage storage are also offered.

Days Inn & Suites by Wyndham Romeoville

per person

Jun 3 - Jun 9

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the business center, express check-in, and conference space. There's a gym on site, and a 24-hour front desk and express check-out are also provided.

Top Chicago hotels deals

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$175

includes taxes & fees

$149 per night

Apr 30 - May 1

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.

Swissotel - Chicago

323 E Wacker Dr, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$235

includes taxes & fees

$200 per night

May 2 - May 3

This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$189

includes taxes & fees

$161 per night

Apr 30 - May 1

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.

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street, Chicago, IL

Free Cancellation

$148

includes taxes & fees

$126 per night

May 4 - May 5

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.

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$200

includes taxes & fees

$170 per night

May 1 - May 2

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.

River Hotel

75 East Wacker Drive, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$173

includes taxes & fees

$147 per night

May 11 - May 12

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.

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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

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Frequently asked questions

How much are vacation packages to Chicago?

Get ready to be surprised — you can vacation in Chicago for as low as $348. At Travelocity, we save you money and hassle with our excellent vacation packages. With hotels, flights and tours all in one place, why wait any longer?

How long should my Chicago vacation be?

Typically, 2 nights is what most tourists book for their Chicago trip. That’s a good starting point, but there’s plenty more to discover if you allow yourself a little longer.

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

Picking up the best package deal to Chicago is a piece of cake with Travelocity. With 400 air carriers and 1,000,000 properties all over the world, you’re spoiled for choice when it comes to your hotels and flights.

Why should I purchase my Chicago vacation bundle via Travelocity?

Because you’ll never roam alone if you book with us, and we offer round-the-clock support and exceptional service to boot. Add to that our Price Match Guarantee and tons of destinations to pick from. It’s our job to make your daydreams a reality.

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

Absolutely — combine your flight, car and hotel into a Chicago vacation package and you can save a tidy sum. With so much to see in Chicago, having your own wheels will make exploring a joy. Once you’ve buckled yourself in, hit the wide open road and cruise toward Six Flags Great America, a famous attraction roughly 35 mi from Chicago.

Which airport is best for Chicago?

O’Hare Intl. Airport (ORD) (16 mi away from downtown), Midway Intl. Airport (MDW) (9 mi away from central Chicago) and Lewis University Airport (LOT) (30 mi away from central Chicago) are the main hubs in Chicago.

What is there to do in Chicago?

While hopping off the tourist trail is rewarding, you really shouldn’t miss the popular sights that make a place famous. Wrigley Field and Six Flags Great America are a couple of them in Chicago.

Where should I stay when visiting Chicago?

If you’re after someplace comfortable to lay your head, have a look at the Congress Plaza Hotel. It’s the top choice for many visitors.

Where to stay in Chicago: Best areas for travelers

Downtown Chicago: Full of atmosphere and ambiance, this is a perfect match if you love being in the thick of the action. Choose a comfortable room at the theWit Chicago - a DoubleTree by Hilton Hotel, the Renaissance Chicago Downtown Hotel or the Cambria Hotel Chicago Loop - Theatre District. Then, you'll be ideally placed to discover this neighborhood's best attractions, like Navy Pier and Chicago Children's Museum.
Near North Side: You've got lots of options when it comes to welcoming places to stay in this neighborhood. To start with, look up the Waldorf Astoria Chicago, The Talbott Hotel and the FieldHouse Jones. You'll be able to jump out of bed and be at terrific attractions like Navy Pier soon after.
Lakeview: If the reason for your travels is to check off the major attractions, staying here is a wise choice. Make yourself comfortable at The Wheelhouse Hotel, the City Suites Hotel or the Best Western Plus Hawthorne Terrace Hotel. Of the area's many highlights, the crowd favorite is Wrigley Field.
West Town: If you're on the hunt for someplace to stay in this area, the Ruby Room , the Beautiful Modern Bright And Open West Town Single Family Home and The Robey are convenient options. Creative types in particular will enjoy this part of town, with Ukrainian Institute Of Modern Art and Chicago Center for the Performing Arts among the many sights available here.
The Loop: If you only have time to discover one attraction in this neighborhood, make a beeline for Millennium Park. Take in this well-known sight at your own pace and then head on back to the Palmer House a Hilton Hotel. The Congress Plaza Hotel and the Chicago Athletic Association also have everything you need for a pleasant stay.