As a matter of fact, you CAN enlarge the root filesystem while Ubuntu is running (I

learned this recently myself here) - this sounds incredible but it's true :)

Here's the list of steps for a simple scenario where you have two partitions, /dev/sda1 is
an ext4 partition the OS is booted from and /dev/sdb2 is swap. For this exercise we
want to remove the swap partition an extend /dev/sda1 to the whole disk.

1. As always, make sure you have a backup of your data - since we're going to
modify the partition table there's a chance to lose all your data if you make a
typo, for example.
2. Run sudo fdisk /dev/sda
○ use p to list the partitions. Make note of the start cylinder of
/dev/sda1
○ use d to delete first the swap partition (2) and then the /dev/sda1
partition. This is very scary but is actually harmless as the data is
not written to the disk until you write the changes to the disk.
○ use n to create a new primary partition. Make sure its start
cylinder is exactly the same as the old /dev/sda1 used to have.
For the end cylinder agree with the default choice, which is to
make the partition to span the whole disk.
○ use a to toggle the bootable flag on the new /dev/sda1
○ review your changes, make a deep breath and use w to write the
new partition table to disk. You'll get a message telling that the
kernel couldn't re-read the partition table because the device is
busy, but that's ok.
3. Reboot with sudo reboot. When the system boots, you'll have a smaller
filesystem living inside a larger partition.
4. The next magic command is resize2fs. Run sudo resize2fs /dev/sda1 -
this form will default to making the filesystem to take all available space on
the partition.

That's it, we've just resized a partition on which Ubuntu is installed, without booting from
an external drive.