Douglas Holidays

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  • Better together

    Save up to €350 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €507, price is now €359 per person
€359
per person
9 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
The staff were extremely impressed and helpful. Help me with restaurant choices, where to go for tours. Only thing I regretted was not packing the proper clothes for the chance of weather. It was my personal birthday present to me and I did enjoyed myself.

Reviewed on 24 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €752, price is now €543 per person
€543
per person
9 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great staff, full kitchen and living room, good location, friendly people, safe. I would stay here again.

Reviewed on 23 Apr 2026

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €571, price is now €418 per person
€418
per person
9 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (1,006 reviews)
The rooms are nice. I was a little disappointed to find out there would be a hold of 80 dollars each day on a credit card

Reviewed on 14 Apr 2026

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
Save 100% on your flight
Price was €575, price is now €425 per person
€425
per person
9 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)
Staff and housekeeping were great! Location was convenient to the blue line. Would stay here again!

Reviewed on 23 Apr 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €625, price is now €464 per person
€464
per person
9 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,417 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.

Reviewed on 14 Apr 2026

Where to stay in Douglas

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

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Top hotels in Douglas

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is €116 per night from 26 Apr to 27 Apr
€116
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,133 reviews)
wifi wouldn’t connect, when we called the front desk to ask (I had work I needed to do, and specifically checked before booking that the room included wifi) was met with attitude to “just connect” even though the wifi network wasn’t visible or available. also, you have no control over the temperature ...

Reviewed on 24 Apr 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is €120 per night from 26 May to 27 May
€120
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (5,123 reviews)
Wonderful and helpful sstaff. Excellent location

Reviewed on 24 Apr 2026

River Hotel
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is €114 per night from 26 May to 27 May
€114
26 May - 27 May
includes taxes & fees
8.2/10 Very Good! (2,636 reviews)
The staff were extremely impressed and helpful. Help me with restaurant choices, where to go for tours. Only thing I regretted was not packing the proper clothes for the chance of weather. It was my personal birthday present to me and I did enjoyed myself.

Reviewed on 24 Apr 2026

Hotel Felix River North/Magnificent Mile
See all 4,733 properties in Douglas
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 Douglas holiday package cost?
Tailor make your Douglas holiday package from as little as €359. Pick from any combination of hotels, flights and rental cars to craft the escape you've been dreaming of. Remember to add on a few experiences or activities!
How do I get a cheap travel package to Douglas?
It's easy. Just bundle. Hotels, rental cars and flights — combine whatever you need into a Douglas holiday package and save. Score even more discounts when you include extras such as experiences or tours to your booking. But that's not the only impressive part. You have the freedom to tailor your trip your way. We offer over 550 airlines and 1,000,000 hotel options globally, so that everyone has an opportunity to travel and live out those holiday dreams.
Where should I stay in Douglas?
Urban explorers come from near and far to experience University of Chicago and Chicago Museum of Science and Industry in Douglas. Book yourself a room close to these popular attractions to make sightseeing easy.
What are the top hotels in Douglas?
Get your trip off to a flying start by booking a stay at Mccormick Place Guest House. It's one of most popular properties in Douglas. Another leading option is Villa Dubois Guest House.
How far in advance should I book my Douglas holiday?
It can be difficult to know exactly when the best time is to book your Douglas holiday. But generally the earlier you book, the cheaper the prices. In some cases, you can lock in your flights and hotels up to a year prior to departure. If you're considering a last-minute getaway, no need to fret! There are terrific deals popping up on Expedia every day.
What does an Expedia Douglas travel package include?
Flights, hotels and a shiny set of wheels for all your road trip adventures. Simply pick and choose your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of tours and experiences and watch your savings stack up. When it comes to crafting your Douglas trip, you're in control!
What should I know before booking a Douglas travel package?
Booking all the parts of your trip together is an excellent way to save. Bundle your car rentals, airfares and hotels into a neat little package. But hotels aren't your only option. Expedia features all sorts of properties, including holiday rentals such as beachside villas and spacious residences. You've got loads of choices!
Can I choose my airline with a Douglas Expedia holiday package?
Yes, you can. We have more than 550 partner airlines all over the world, so choose the carrier that's a good fit for your travel needs.
If I'm not able to travel, can I cancel my Douglas holiday package?
Yes, you can. We get that things don't always go to plan, so we're here to help if you have to make changes to your Douglas holiday package. You may be able to cancel or change your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Popular places to visit

Lake Meadows Park

Lake Meadows Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its fascinating museums.

Lake Meadows Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

€38
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
94% of travellers recommend
Art Institute of Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.