11 days in Hawaii & Chicago Itinerary

11 days in Hawaii & Chicago Itinerary

Created using Inspirock United States trip maker

Plan created by another user. Make it yours
1
Honolulu, Oahu
— 3 nights
2
Kihei, Maui
— 3 nights
3
Chicago
— 4 nights

S M T W T F S
11
12
13
14
15
16
17
18
19
20
21
22
23
24

3
nights
Honolulu, Oahu

Honolulu ©

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
You'll visit kid-friendly attractions like USS Arizona Memorial and Kailua Beach Park. There's still lots to do: enjoy the sand and surf at Waikiki Beach, discover the deep blue sea with a scuba or snorkeling tour, explore the activities along Hanauma Bay Nature Preserve, and tour the pleasant surroundings at Puu Ualakaa State Park.

For photos, maps, more things to do, and tourist information, refer to the Honolulu route planning website.

Moline to Honolulu is an approximately 12-hour flight. Traveling from Moline to Honolulu, you'll gain 4 hours due to the time zone difference. Expect much warmer temperatures when traveling from Moline in October; daily highs in Honolulu reach 87°F and lows reach 74°F. Wrap up your sightseeing on the 17th (Sat) early enough to travel to Kihei.

Things to do in Honolulu

Side Trip

Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach
Diamond Head State Monument ©
Diamond Head State Monument

3
nights
Kihei, Maui

Kihei ©
Stretching over 9.7 km (6 mi) of pristine south Maui coastline, Kihei is the island's driest and sunniest region, making it a perfect location for water activities and beach leisure.
Start off your visit on the 18th (Sun): admire nature's wide array of creatures at Maui Ocean Center, discover the deep blue sea with a scuba or snorkeling tour, then test your team's savvy at Maui Escape Rooms, and finally kick your exploration up a notch at some of the top local zipline courses and adventure parks. Get ready for a full day of sightseeing on the 19th (Mon): steep yourself in history at Wo Hing Temple Museum, then walk around Lahaina Banyan Court, and then tour the pleasant surroundings at Ka'anapali Beach.

To find photos, traveler tips, more things to do, and more tourist information, read Kihei trip itinerary builder app.

Fly from Honolulu to Kihei in 3 hours. Expect a daytime high around 88°F in October, and nighttime lows around 70°F. Wrap up your sightseeing on the 20th (Tue) to allow time to travel to Chicago.

Things to do in Kihei

Parks · Outdoors · Beaches · Zoos & Aquariums

Side Trips

Highlights from your plan
Maui Escape Rooms ©
Maui Escape Rooms
Maui Ocean Center ©
Maui Ocean Center
Ka'anapali Beach ©
Ka'anapali Beach

4
nights
Chicago

Chicago ©

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kids will enjoy The Art Institute of Chicago and Millennium Park. There's lots more to do: engage your brain at Museum of Science and Industry, get up close and personal with brilliant marine life at Shedd Aquarium, make a trip to Buckingham Fountain, and take a stroll through The Magnificent Mile.

To see more things to do, traveler tips, photos, and other tourist information, read our Chicago trip itinerary maker tool.

You can fly from Kihei to Chicago in 13.5 hours. Due to the time zone difference, you'll lose 4 hours traveling from Kihei to Chicago. Plan for cooler temperatures traveling from Kihei in October, with highs in Chicago at 65°F and lows at 49°F. Finish your sightseeing early on the 24th (Sat) to allow enough time to travel back home.

Things to do in Chicago

Museums · Parks · Childrens Museums · Zoos & Aquariums
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry
Shedd Aquarium ©
Shedd Aquarium

Similar plans

15 days in Hawaii BY A USER FROM UNITED STATES May, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, fast-paced, popular & hidden gems Preferences: May, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Fast-paced 15 days in Hawaii BY A USER FROM CANADA January, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife, popular & hidden gems Preferences: January, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Medium 14 days in Hawaii BY A USER FROM UNITED STATES September, culture, relaxing, romantic, beaches, shopping, wildlife, slow & easy, popular & hidden gems Preferences: September, culture, relaxing, romantic, beaches, shopping, wildlife Attraction style: Popular & hidden gems Pace: Slow & easy 15 days in Hawaii BY A USER FROM UNITED KINGDOM March, culture, outdoors, relaxing, beaches, shopping, wildlife, popular & hidden gems Preferences: March, culture, outdoors, relaxing, beaches, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 10 days in Chicago BY A USER FROM UNITED STATES February, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: February, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 22 days in Illinois BY A USER FROM UNITED STATES June, teens, culture, outdoors, relaxing, romantic, beaches, shopping, wildlife, fast-paced, hidden gems Preferences: June, teens, culture, outdoors, relaxing, romantic, beaches, shopping, wildlife Attraction style: Hidden gems Pace: Fast-paced 12 days in United States BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, hidden gems Preferences: September, culture, outdoors, relaxing, romantic, beaches, historic sites Attraction style: Hidden gems Pace: Medium 12 days in United States BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, hidden gems Preferences: September, culture, outdoors, relaxing, romantic, beaches, historic sites Attraction style: Hidden gems Pace: Medium 12 days in United States BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, hidden gems Preferences: September, culture, outdoors, relaxing, romantic, beaches, historic sites Attraction style: Hidden gems Pace: Medium 16 days in Hawaii BY A USER FROM UNITED STATES March, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, popular & hidden gems Preferences: March, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium
See more plans