Downtown Chicago Holiday Packages - Save on Downtown Chicago Flight & Hotel

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

Level Chicago Fulton Market

Downtown Chicago

฿237,985

per person

30 Aug - 5 Sept

found 1 day ago

Return flight included

Bangkok (DMK) to Chicago (ORD)

9.2/10 Wonderful! (512 reviews)

Location

Reviewed on 10 Jul 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

฿261,820

per person

30 Aug - 5 Sept

found 1 day ago

Return flight included

Bangkok (DMK) to Chicago (ORD)

9.6/10 Exceptional! (1,910 reviews)

I love Trump hotels the absolute BEST

Reviewed on 10 Jul 2026

The Peninsula Chicago

Downtown Chicago

฿273,427

per person

30 Aug - 5 Sept

found 1 day ago

Return flight included

Bangkok (DMK) to Chicago (ORD)

9.8/10 Exceptional! (1,008 reviews)

The most helpful staff. The most comfortable bed. The most luxurious bathroom. The Peninsula is unrivaled amongst the five-star hotels. Cannot wait to return yet again!

Reviewed on 5 Jul 2026

The Langham, Chicago

Downtown Chicago

฿257,882

per person

30 Aug - 5 Sept

found 1 day ago

Return flight included

Bangkok (DMK) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Fantastic staff, beautiful property. Highly recommend the club lounge

Reviewed on 10 Jul 2026

Nobu Hotel Chicago

Downtown Chicago

฿264,595

per person

30 Aug - 5 Sept

found 1 day ago

Return flight included

Bangkok (DMK) to Chicago (ORD)

9.4/10 Exceptional! (879 reviews)

Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.

Reviewed on 6 Jul 2026

Where to stay in Downtown Chicago

Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Chicago

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

Top hotels in Downtown Chicago

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

฿5,124

฿6,092 total

27 Jul - 28 Jul

includes taxes & fees

8.2/10 Very good! (1,735 reviews)

"Great location, clean, and a super breakfast!"

Reviewed on 11 Jul 2026

Omni Chicago Hotel

676 N Michigan Ave Chicago IL

฿7,425

฿9,936 total

26 Jul - 27 Jul

includes taxes & fees

9.2/10 Wonderful! (1,909 reviews)

"Great hotel with perfect and safe location. I loved the suite room with separate coach very roomy! The staff are the best, and the breakfast is great. Highly recommend this hotel!"

Reviewed on 12 Jul 2026

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

฿6,292

฿7,481 total

10 Aug - 11 Aug

includes taxes & fees

8/10 Very good! (10,230 reviews)

"Older hotel, but nice"

Reviewed on 11 Jul 2026

See all 1,556 properties in Downtown Chicago

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.

Frequently asked questions

How much does a Downtown Chicago holiday package cost?

Go from looking to booking with our Downtown Chicago holiday packages, which start from just ฿237,985. Handpick the hotels and flights that suit your travel style. Then, add on a couple of tours or activities for an amazing adventure.

How do I get a cheap travel package to Downtown Chicago?

Bundle your bookings with Expedia to save big on your next trip. With more than 550 partner airlines and 1,000,000 hotels across the world, your Downtown Chicago holiday package can be tailored exactly to suit your budget. With all that extra money, why not include one or two fun tours and activities? It's an easy way to unlock even more savings. The holiday you've always dreamed of in Downtown Chicago is much closer than you thought!

How far in advance should I book my Downtown Chicago holiday?

While not all airlines advertise tickets early, you can normally look up international airfares on Expedia up to 12 months in advance. This is the time you'll score some incredible deals. If you've left things to the last minute, you could still be in luck. Discounted prices occasionally emerge a few weeks before departure.

What does an Expedia Downtown Chicago travel package include?

Packages include flights, hotels and rental cars, but you can mix and match them to create your ideal Downtown Chicago trip. You can also add on fun things like activities and tours once you've made your booking. You're in charge! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere.

What should I know before booking a Downtown Chicago travel package?

Our prices are always low. However, you'll pick up even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice.

Can I choose my airline with a Downtown Chicago Expedia holiday package?

Yes — that's the beauty of an Expedia holiday package. You're in charge! We have more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Downtown Chicago trip.

If I'm not able to travel, can I cancel my Downtown Chicago holiday package?

You can. We understand that even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Downtown Chicago holiday package. You may be able to change or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.