Grand Boulevard Vacation Packages from $462

Grand Boulevard flight + hotel vacation packages

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

JW Marriott Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 25 - Jul 29

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 business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Save 100% on your flight

per person

Jun 14 - Jun 17

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the gym, poolside bar, and concierge services.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

per person

Jul 25 - Jul 29

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 and free WiFi in public areas. Self parking, a lobby fireplace, and a communal living room are also offered.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 25 - Jul 29

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. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Fairmont Chicago at Millennium Park Gold Experience

Downtown Chicago

Save 100% on your flight

per person

Jun 17 - Jun 20

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 business center and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and express check-in are also provided.

Top Grand Boulevard hotel deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$167

per night

May 27 - May 28

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

Warwick Allerton - Chicago

701 North Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$125

per night

May 28 - May 29

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-in, and valet parking.

Pet friendly

Parking available

The Westin Michigan Avenue Chicago

909 North Michigan Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$181

per night

May 13 - May 14

A full-service spa, a 24-hour gym, 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 gym, bar/lounge, and coffee shop.

Pet friendly

Breakfast available

River Hotel

75 East Wacker Drive, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$159

per night

May 12 - May 13

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

Aloft Chicago Mag Mile

243 E. Ontario, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$149

per night

May 12 - May 13

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Valet parking, a business center, and a snack bar/deli are also offered.

Pet friendly

Breakfast available

Eurostars Magnificent Mile

660 North State Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$180

per night

May 13 - May 14

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

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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

Harold Washington Cultural Center

You can enjoy some culture when you stop by Harold Washington Cultural Center in Chicago. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

Elam House

You can learn about the history of Chicago when you stop by Elam House. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

Dr. Daniel Hale Williams Residence

You can learn about the history of Chicago with a trip to Dr. Daniel Hale Williams Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

Photos of local treasures

Frequently asked questions

How much are vacation packages to Grand Boulevard?

Starting from as little as $462, flight and hotel packages are an excellent way to make your vacation budget stretch further. Watch out Grand Boulevard — here you come!

Where can I get the best vacation package deals for Grand Boulevard?

You can’t beat Travelocity when it comes to putting together your Grand Boulevard package deal. There are as many as 400 airlines and 1,000,000 properties worldwide to select from. Book your trip now and get ready to cross another exciting place off your list.

Why should I purchase my Grand Boulevard vacation package via Travelocity?

Nothing tops the peace of mind knowing you’ve bagged the best deal around — that’s our Price Match Guarantee. Add to that our enormous range of destinations and 24/7 team of customer service professionals and you’ve got the blueprint for a hassle-free vacation.

Can I save money on my Grand Boulevard car rental if I book it with a hotel or flight?

Sure can — and booking one of our Grand Boulevard vacation packages is the easiest way to do this. Bundle any combination of a hotel, car, flight and experience and land great discounts. The more you book, the more you’ll save. There are so many impressive sights in and around Grand Boulevard to put on your bucket list, including Six Flags Great America (40 mi from Grand Boulevard). Nothing beats discovering thrilling places like this with the freedom of your own car rental.

What is the best time of year to go to Grand Boulevard?

If you need to watch your pennies, is the perfect month to explore Grand Boulevard, while is the dearest time of the year. March, May and August is high season. If you’re looking to avoid the big crowds, January, September and December tend to be quieter.