Chicago Vacation Packages 2026 from $426

Chicago flight + hotel vacation packages

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

The Whitehall Hotel, BW Premier Collection

Downtown Chicago

Save 100% on your flight

$426

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a computer station, and dry cleaning are also offered.

Four Seasons Hotel Chicago

Downtown Chicago

$2,475

per person

Sep 13 - Sep 19

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 smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$856

per person

Sep 25 - Sep 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$1,081

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$817

per person

Sep 25 - Sep 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Stay near popular Chicago attractions

An aerial view of a baseball stadium surrounded by urban buildings.

Wrigley Field

9.0/10 (11,704 reviews)

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

See properties

Frequently asked questions

How much are vacation packages to Chicago?

Get ready to be surprised — you can vacation in Chicago for as low as $426. 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.