$89 Cheap flight deals from Dubuque (DBQ) to Chicago (CHI)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Dubuque to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, May 4 - Thu, May 8
DBQ
Dubuque Regional
ORD
O'Hare Intl.
$202 Roundtrip, found 6 days ago
$202
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, May 4 from Dubuque Regional to O'Hare Intl., returning Thu, May 8, priced at $202 found 6 days ago

Airfares from $89 One Way, $178 Round Trip from Dubuque to Chicago

Prices starting at $178 for return flights and $89 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Aug 29 - Fri, Sep 5
DBQ
Dubuque
ORD
Chicago
$178 Roundtrip, found 13 hours ago
$178
Roundtrip
found 13 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Aug 29 from Dubuque to Chicago, returning Fri, Sep 5, priced at $178 found 13 hours ago
Fri, Jun 27 - Sun, Jun 29
DBQ
Dubuque
ORD
Chicago
$180 Roundtrip, found 2 days ago
$180
Roundtrip
found 2 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Jun 27 from Dubuque to Chicago, returning Sun, Jun 29, priced at $180 found 2 days ago
Fri, May 16 - Fri, May 23
DBQ
Dubuque
ORD
Chicago
$181 Roundtrip, found 1 day ago
$181
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, May 16 from Dubuque to Chicago, returning Fri, May 23, priced at $181 found 1 day ago
Thu, May 8 - Sat, May 17
DBQ
Dubuque
ORD
Chicago
$190 Roundtrip, found 4 hours ago
$190
Roundtrip
found 4 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, May 8 from Dubuque to Chicago, returning Sat, May 17, priced at $190 found 4 hours ago
Fri, May 9 - Tue, May 13
DBQ
Dubuque
ORD
Chicago
$191 Roundtrip, found 2 days ago
$191
Roundtrip
found 2 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, May 9 from Dubuque to Chicago, returning Tue, May 13, priced at $191 found 2 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel
3.5-star property

Congress Plaza Hotel

7.8/10 Good! (8,642 reviews)

Jun 12 - Jun 17

5 night stay

Dubuque (DBQ) to Chicago (ORD)

Denver Air Connection • Roundtrip • Coach
Save 100% on your flight
per person
found 8 hours ago
Propert is near Lake Michigan and walkable to Blue/Red lines. However, room was so hot, could not adjust temperature in the room so you’re at the mercy of the weather. Had to open our windows at night which didn’t help much but also created so much noise from traffic outside. The last night the staff came to room voluntarily to give us a fan due to excessive heat and temperature outside was only in low 60s. Otherwise convenient and cheap, just uncomfortable sleeping conditions.

Reviewed on Apr 19, 2025

Arlo Chicago
4.0-star property

Arlo Chicago

9.2/10 Wonderful! (1,665 reviews)

Jun 12 - Jun 17

5 night stay

Dubuque (DBQ) to Chicago (ORD)

Denver Air Connection • Roundtrip • Coach
Save 100% on your flight
per person
found 8 hours ago
Nice hotel. Great location. Nice room. Pictures made hotel seem like it was so much more. It was just one small hallway. Nothing more. Very disappointed with the lobby. I thought by the pictures I was getting so much more! Payed a $150 resort fee for two night. There was absolutely no resort and no resort benefits. That was purely a money grab. Didn’t even get my room cleaned each day. Nice room. Nice hotel. Just less that I thought!

Reviewed on Oct 13, 2024

Virgin Hotels Chicago
4.5-star property

Virgin Hotels Chicago

9.2/10 Wonderful! (1,320 reviews)

Jun 12 - Jun 17

5 night stay

Dubuque (DBQ) to Chicago (ORD)

Denver Air Connection • Roundtrip • Coach
Save 100% on your flight
per person
found 8 hours ago
Absolutely loved this property. Super convenient, the metro and train stations a very short walk away. Right by the bean and river north. Cafe and commons club were fantastic, service was great by all staff.

Reviewed on Apr 6, 2025

Don't see what you're looking for?
See all available trips from Dubuque to Chicago
View all trips

More About Flying To Chicago from Dubuque

Route Information for Flights from Dubuque to Chicago

Origin Airport IATA Code
DBQ
Destination Airport IATA Code
CHI
Distance
146 mi
Direct Flight Airlines
Earliest Flight Arrival
9:50PM UTC
Latest Flight Arrival
9:50PM UTC

Dubuque to Chicago

Smart business means on-the-spot travel planning at budget prices. Orbitz On-the-Go can help by using cutting-edge mobile tools and guaranteed low prices. Orbitz On-the-Go is your go-to for bargain flights from Dubuque to Chicago, and discount Dubuque to Chicago flights.

Business Development

Boosting sales with multiple presentations within a day or week? Then easily book cheap domestic flights from Dubuque to Chicago. Are you expanding into emerging markets? Find low-fare deals on international Dubuque to Chicago flights. Orbitz On-the-Go mobile apps keep it simple.

Continuing Education

Successful business people know that keeping your edge in business means staying in training. Find a low-cost air ticket for your next workshop with Orbitz flights from Dubuque to Chicago. Move to the head of the seminar with Orbitz On-the-Go’s guaranteed low prices on Dubuque to Chicago flights.

Budget Planning

Orbitz allows you to focus on the income, while we reduce your expenses with guaranteed low prices. Your bottom line is bound to improve with our bargain flights from Dubuque to Chicago and discount Dubuque to Chicago flights. Watch your business thrive.

Time Management

Time is money, and Orbitz On-the-Go saves both. Our cutting-edge mobile tools make business travel planning quick and easy, even for same-day reservations. It’s not unusual for our clients to save big on same-day tickets for Dubuque to {destination.name} flights. Free alerts keep you on time with flight, gate and baggage updates, plus other time-saving features.

Frequently asked questions

Are there non-stop flights from Dubuque to Chicago?
American Airlines flies directly from Dubuque to Chicago, so all you need to do is kick back and relax until you reach O’Hare Airport.
What is the shortest flight from Dubuque to Chicago?
It can take as little as 1 hour and 8 minutes to get from Dubuque Regional Airport to Chicago, IL (ORD-O’Hare Intl.). Take a seat and enjoy those window views, because you’ll be disembarking before long.
What airlines fly from Dubuque to Chicago most frequently?
American Airlines is the most frequent flyer along this route. This trusted airline operates 60 flights from Dubuque, IA (DBQ-Dubuque Regional) to O’Hare Airport each month.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.