East Side Vacation Packages from $644

East Side flight + hotel vacation packages

JW Marriott Chicago

Downtown Chicago

per person

Jun 28 - Jun 30

Roundtrip flight included

Dallas (DAL) 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.

Fairmont Chicago at Millennium Park Gold Experience

Downtown Chicago

Save 100% on your flight

per person

May 23 - May 26

Roundtrip flight included

Dallas (DFW) 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 and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and express check-in are also provided.

Park Hyatt Chicago

Downtown Chicago

per person

Jun 28 - Jun 30

Roundtrip flight included

Dallas (DAL) 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

per person

Jun 28 - Jun 30

Roundtrip flight included

Dallas (DAL) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Level Chicago – Old Town

Downtown Chicago

per person

Jun 28 - Jun 30

Roundtrip flight included

Dallas (DAL) to Chicago (ORD)

A full-service spa and A 24-hour gym are featured at this smoke-free aparthotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and perks like free WiFi.

Prices and availability subject to change. Additional terms may apply.

Top East Side hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$127

per night

Apr 28 - Apr 29

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

75 East Wacker Drive, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$129

per night

Apr 21 - Apr 22

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

Eurostars Magnificent Mile

660 North State Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$150

per night

Apr 23 - Apr 24

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.

Spa

Parking available

Hotel Felix River North/Magnificent Mile

111 W Huron St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$91

per night

Apr 21 - Apr 22

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

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$119

per night

Apr 21 - Apr 22

A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A snack bar/deli, express check-in, and express check-out are also on offer.

Pet friendly

Breakfast available

InterContinental Chicago Magnificent Mile, an IHG Hotel

505 N Michigan Ave, Chicago, IL

Free Cancellation

$199

per night

Apr 21 - Apr 22

This historic hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. You'll appreciate the steam room, bar/lounge, and coffee shop.

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

Calumet Park

4/5(1 review)

Explore the great outdoors at Calumet Park, a lovely green space in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.

Calumet Beach

Why not spend a lazy afternoon at Calumet Beach during your trip to Chicago? While you're in the area, wander around the parks.

Munson Beach

Why not spend a lazy afternoon at Munson Beach during your trip to Chicago? While you're in the area, wander around the parks.

Frequently asked questions

How much are vacation packages to East Side?

$644 is all you’ll need for a memorable escape in East Side. Bundle your flights and hotel into a Travelocity vacation package and see the savings add up. With these kinds of prices, traveling has never been so accessible.

Where can I get the best vacation package deals for East Side?

With at least 400 airlines and 1,000,000 hotels across the world, it’s tough to beat Travelocity. Scroll through our extensive range and grab an affordable East Side vacation package. Don’t you love it when travel is that easy?

Why should I book my East Side vacation bundle with Travelocity?

With fantastic service, 24/7 customer support and some of the most incredible getaways imaginable, you’ll never roam alone. And if you find a lower price, we’ll match it. That’s our Price Match Guarantee.

Will I save money on my East Side car rental if I bundle it with hotels and flights?

Absolutely — and if you also add an experience or a tour to your East Side vacation package, you’ll save even more. With one of our affordable packages, you can find things to do around the region that are right up your alley. Then, jump in your rental car and work your way through the list. Six Flags Great America is one must-see attraction to visit. It’s 50 mi from East Side.

What is the best time of year to go to East Side?

Head off in and spend more cash on awesome experiences, not your hotel. This is the most cost-effective month to arrange your stay. Prices are at their highest in , so avoid traveling during this time if you’re eager to save. March, May and August is the peak period in East Side. You’ll need to book ahead of time and be prepared to pay higher prices. January, September and December are the quietest months.

What is there to do in East Side?

Calumet Park and Calumet Beach have captivated so many travelers. Check these popular attractions off your must-see list and discover what the hype is about.